4,4-Dimethoxybut-1-yne

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4,4-Dimethoxybut-1-yne: 1-butyne, 4,4-dimethoxy-; 4,4-Dimethoxy-1-butyne; 4,4-Dimethoxybut-1-yne; (1) (33639-45-1)



4,4-Dimethoxybut-1-yne (1) has the following physical and spectroscopic properties: bp 62-67 °C (75 mmHg);

¹H NMR (CDCl₃, 600 MHz)
δ 2.03 (t, J = 2.7 Hz, 1 H),TRIPLE BOND H
2.53 (dd, J = 5.6, 2.7 Hz, 2 H), CH2
3.38 (s, 6 H), TWO METHOXY
4.55 (t, J = 5.6 Hz, 1 H).      O-CH-O

  

¹³C NMR (CDCl₃, 150 MHz) δ: 23.7, 53.4, 70.2, 79.3, 102.3.

HRMS (ESI) m/z: Calcd. for C₆H₁₀O₂ [M+Na]⁺: 137.0573, found: 137.0573.

IR (cm^-1): 3289, 2938, 2834, 2124, 1447, 1423, 1362, 1240, 1192, 1120, 1064.

Anal. calcd for C₆H₁₀O₂: C, 63.14; H, 8.83. Found: C, 62.86; H, 8.86.






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(S)-tert-Butyl 2-(benzylcarbamoyl)pyrrolidine-1-carboxylate

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 (S)-tert-Butyl 2-(benzylcarbamoyl)pyrrolidine-1-carboxylate

Boc-L-proline
Boc-L-Proline: Boc-Pro-OH, N-(tert-Butoxycarbonyl)-L-proline; (15761-39-4)

benzylamine
Benzylamine: α-Aminotoluene; (100-46-9)

IR (neat) 3310, 2976, 2871, 1682, 1652, 1526, 1393, 1370, 1157, 1127, 766, 724, 693 cm^-1. mp 124-125 °C.  

¹H NMR (600 MHz, d-6 DMSO)

Major rotamer δ: 1.28 (s, 6 H), 1.41 (s, 3 H), 1.67 - 1.90 (m, 3 H), 2.04 - 2.18 (m, 1 H), 3.25 - 3.32 (m, 1 H), 3.36 - 3.43 (m, 1 H), 4.08 (dd, J = 8.6, 3.1 Hz, 1 H), 4.21 (dd, J = 14.0, 5.9 Hz, 1 H), 4.34 (dd, J = 14.0, 5.9 Hz, 1 H), 7.20-7.34 (m, 5 H), 8.39 (t, J = 5.9 Hz, 1 H).

Minor rotamer δ: 1.28 (s, 6 H), 1.41 (s, 3 H), 1.67 - 1.90 (m, 3 H), 2.04 - 2.18 (m, 1H), 3.25 - 3.32 (m, 1 H), 3.36 - 3.43 (m, 1 H), 4.12 (dd, J = 8.6, 3.1 Hz, 1 H), 4.19 (dd, J = 14.0, 5.9 Hz, 1 H), 4.34 (dd, J = 14.0, 5.9 Hz, 1 H), 7.20-7.34 (m, 5 H), 8.34 (t, J = 5.9 Hz, 1 H).  

¹H NMR (600 MHz, DMSO, 60 °C) δ: 1.29 (s, 9 H), 1.67 - 1.91 (m, 2 H), 1.99 - 2.20 (m, 1 H), 3.29 (dt, J = 10.5, 6.8 Hz, 1 H), 3.38 (ddd, J = 10.5, 7.5, 5.1 Hz, 1 H), 4.10 (s, 1 H), 4.21 (dd, J = 14.9, 6.0 Hz, 1 H), 4.31 (dd, J = 14.9, 6.0 Hz, 1 H), 7.20 (t, J = 6.8 Hz, 1 H), 7.23 - 7.31 (m, 4 H), 8.16 (s, 1 H).


¹³C NMR (150 MHz, d-6 DMSO)

Major rotamer δ: 23.6, 28.4, 31.6, 42.5, 47.0, 60.4, 78.9, 127.8, 128.6, 140.1, 153.8, 172.9;

Minor rotamer δ: 24.5, 28.66, 30.5, 42.3, 47.2, 60.3, 79.1, 127.0, 127.19, 127.3, 140.1, 154.2, 172.7.

HRMS m/z calcd for C₁₇H₂₅N₂O₃ [M + H]⁺: 305.1860; Found: 305.1856. Anal. calcd for C₁₇H₂₄N₂O₃: C, 67.08; H, 7.95; N, 9.20; Found: C, 67.02; H, 7.89; N, 9.04.

Chiral HPLC AD-H column, 90:10 isohexane:2-PrOH, flow 0.7 mL/min, 30 °C, retention time 18.54 min (Retention times for racemic sample = 7.16 min and 19.93 min).

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