(1S,4R)-2-(4-Methoxybenzoyl)bicyclo[2.2.2]octa-2,5-diene

 

(1S,4R)-2-(4-Methoxybenzoyl)bicyclo[2.2.2]octa-2,5-diene (3a) Yellow liquid (25.2 mg, 95% yield):

1H NMR (300 MHz, CDCl3)   1.39 (s, 4H, alkyl), 3.77-3.80 (m, 1H, alkyl), 3.85 (s, 3H, OMe), 4.36 (d, J = 5.4 Hz, 1H, alkyl), 6.36 (dd, J = 6.0, 6.0 Hz, 1H, vinyl), 6.46 (dd, J = 6.0, 6.0 Hz, 1H, vinyl), 6.88-6.91 (m, 3H, vinyl + arom.), 7.67 (d, J = 8.3 Hz, 2H, arom.);

13C{1H} NMR (75 MHz, CDCl3)  = 24.7, 24.8, 37.1, 38.2, 55.4, 113.3, 130.8, 131.5, 133.2, 135.1, 146.5, 147.7, 162.6, 192.3;

HRMS (ESI-TOF) m/z calculated for C16H16NaO2 [M+Na]+ 263.1048, found 263.1036;

FT-IR (neat, cm-1 ) 1033, 1174, 1255, 1354, 1600, 1637, 1730, 2870, 2957, 3054.

Optical Rotation: []D 26 +39.9 (c 2.52, CHCl3) for an enantiomerically enriched sample of 94% ee.

HPLC analysis (column, CHIRALPAK AD-3, hexane/2-propanol = 98/2, flow rate 1.0 mL/min, 20 C, detection UV 250 nm light); tR of major-isomer 20.7

Org. Lett., 2018, 20 (23), pp 7353–7357

DOI: 10.1021/acs.orglett.8b02263

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(1S,4R)-2-(4-Methoxybenzoyl)bicyclo[2.2.2]octa-2,5-diene

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Isosorbide-2-acetate

Spectral Data for 1

MS (ESI): calcd for [M + Na]+, 211.11; found, 211.11.

IR (KBr) cm–1: 1732.08 (C═O), 3398.57 (−OH).

1H NMR (400 MHz, CD3OD): δ 5.11 (d, J = 3.6 Hz, 1H), 4.76 (s, 1H), 4.54 (t, J = 4.6 Hz, 1H), 4.49 (d, J = 4.4 Hz, 1H), 4.27 (td, J = 6.7, 5.1 Hz, 1H), 4.01 (dd, J = 10.7, 3.7 Hz, 1H), 3.95 (d, J = 10.7 Hz, 1H), 3.85 (dd, J = 8.8, 6.4 Hz, 1H), 3.50 (dd, J = 8.8, 7.3 Hz, 1H), 2.06 (s, 3H).

13C NMR (101 MHz, CD3OD): δ 20.8, 73.0, 73.7, 74.3, 80.0, 83.4, 86.9, 171.8.

Org. Process Res. Dev., Article ASAP

DOI: 10.1021/acs.oprd.8b00310

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2-amino-4-bromo-5-fluorobenzoic acid

 

2-amino-4-bromo-5-fluorobenzoic acid as a white to off-white crystalline solid

1H NMR (400 MHz, DMSO-d6) δ 7.62 (d, J=9.6 Hz, 1H), 7.21-6.5 (m, 3H), 3.8- 3.3 (br s, 1H).

13C NMR (100 MHz, DMSO-d6) δ 170.5, 149.6, 147.6, 147.3, 120.4, 118.1, 118.0, 109.2, 109.0, 99.5.

mp >250 °C. IR (neat) 3494, 3351, 3053, 3038, 1521, 774 cm-1;

HRMS (ESI) m/z: calcd for C7H5BrFNO2 [M+H]+ 233.9560, found 233.9551.

Org. Lett., 2018, 20 (13), pp 3736–3740

DOI: 10.1021/acs.orglett.8b01218

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Quetiapine

Quetiapine

1H NMR (400 MHz, CD3OD): δ = 3.18-3.27 (m, 4H), 3.35-3.44 (m, 3H), 3.56-3.58 (m, 3H), 3.67-3.69 (m, 3H), 3.76 (t, J = 5.2 Hz, 2H), 4.32 (s, 1H), 6.88 (td, J = 7.4 Hz, 1.2 Hz, 1H), 7.04 (dd, J = 7.8 Hz, 1.6 Hz, 1H), 7.13 (td, J = 7.8 Hz, 1.6 Hz, 1H), 7.23 (dd, J = 6.8 Hz, 2.4 Hz, 1H), 7.28-7.39 (m, 4H) ppm.

13C NMR (100 MHz, CD3OD): δ = 40.2, 45.6, 52.8, 53.3, 57.6, 62.0, 65.6, 73.4, 123.9, 125.99, 126.0, 128.4, 129.0, 130.6, 131.3, 132.5, 133.2, 134.7, 137.9, 145.7, 170.6 ppm.

HRMS (ESI+ ): calcd for C21H26N3O2S [M+H]+ 384.1740, found 384.1735.

Org. Lett., Article ASAP

DOI: 10.1021/acs.orglett.8b02812

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3-fluoro-4- morpholinoaniline

 

3-fluoro-4- morpholinoaniline

1H NMR (400MHz, CDCl3)  6.82 (m, 1H, ArH), 6.43 (m, 2H, 2xArH), 3.87 (m, 4H, 2xCH2O), 3.58 (brs, 2H, NH2), 2.99 (m, 4H, 2xCH2N). 13C NMR (100MHz, CDCl3)  156.9 (d J= 245.4Hz), 143.0 (d J=10.4Hz), 131.8 (d J=9.7Hz), 120.4 (d J=4.2Hz), 110.8 (d J=3.0Hz), 104.0 (d J=23.8Hz), 67.3, 51.9 (d J=2.1Hz). HRMS [M] Calcd for C10H13FN2O 196.1006, Found 196.1004.

 

Org. Process Res. Dev., Article ASAP

DOI: 10.1021/acs.oprd.8b00153

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4-(2-fluoro-4-nitrophenyl)morpholine

 

4-(2-fluoro-4-nitrophenyl)morpholine

1H NMR (400MHz, CDCl3)  8.03 (ddd J=1.0, 2.6 and 9.0Hz, 1H, ArH), 7.94 (dd J=2.6 and 13.1Hz, 1H, ArH), 6.94 (t J=8.7Hz, 1H, ArH), 3.90 (t J=4.7Hz, 4H, 2xCH2O), 3.31 (m, 4H, 2xCH2N).

13C NMR (100MHz, CDCl3)  153.3 (d J=249.5), 145.6 (d J=7.8Hz), 121.1 (d J=3.0Hz), 117.0 (d J=3.9Hz), 112.7 (d J=6.4Hz), 66.7, 50.0 (d J=4.9Hz).

HRMS [M] Calcd for C10H11FN2O3 226.0748, Found 226.0749.

Catalytic Static Mixers for the Continuous Flow Hydrogenation of a Key Intermediate of Linezolid (Zyvox)

James Gardiner, Xuan Nguyen, Charlotte Genet, Mike D. Horne, Christian H. Hornung, and John Tsanaktsidis

 

Org. Process Res. Dev., Article ASAP

DOI: 10.1021/acs.oprd.8b00153

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1-(4-Cyanophenyl)piperazine

1-(4-Cyanophenyl)piperazine

1-(4-Cyanophenyl)piperazine (1a).1 Isolated as a mixture of mono (1a) and di (3) arylated products ~9:1. Conversion: quantitative. Peaks attributed to 1a: 1H NMR (400 MHz, CD3Cl) δH 7.47 (m, 2H, arH), 6.83 (m, 2H, ar-H), 3.26 (m, 4H, pip-H), 2.99 (m, 4H, pip-H), 1.69 (br s, 1H, NH). Peaks attributed to 3: 7.52 (d, J = 9.0 Hz, 4H, ar-H), 6.88 (d, J = 9.0 Hz, 4H, ar-H), 3.29 (s, 8H, pip-H).

Org. Process Res. Dev., Article ASAP

DOI: 10.1021/acs.oprd.8b00090

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https://pubs.acs.org/doi/suppl/10.1021/acs.oprd.8b00090/suppl_file/op8b00090_si_001.pdf