3,4-Pyrrolidinedimethanol, 1-(phenylmethyl)-, (3R,4S)-rel- synthesis
- Product Name:3,4-Pyrrolidinedimethanol, 1-(phenylmethyl)-, (3R,4S)-rel-
- CAS Number:179601-65-1
- Molecular formula:C13H19NO2
- Molecular Weight:221.3
![5-benzyltetrahydro-3aH-furo[3,4-c]pyrrole-1,3-dione](/CAS/20180629/GIF/1221289-17-3.gif)
1221289-17-3
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Yield:179601-65-1 74%
Reaction Conditions:
with lithium aluminium tetrahydride in tetrahydrofuran at 25; for 1 h;
Steps:
(1-Benzylpyrrolidine-3,4-diyl)dimethanols 18a-e
General procedure: To a solution of 17 (0.909 mol) in THF (300 mL) was added to a suspension of LiAlH4 (69 g, 1.82 mol) in THF (1200 mL) dropwise at 25 °C, and the resulting mixture was stirred at rt for 1 h. The reaction was quenched by careful addition of H2O (100 mL), 10% aq KOH (200 mL), and more H2O (100 mL). The precipitate was filtered, washed with THF, and the combined filtrates were evaporated under reduced pressure to give diol 18. cis-(1-Benzylpyrrolidine-3,4-diyl)dimethanol (18a). White solid; yield: 150 g (74%); mp 73-74 °C. 1H NMR (DMSO-d6, 400 MHz): δ = 2.06-2.13 (m, 2 H), 2.24-2.33 (m, 2H), 2.67-2.74 (m, 2 H), 3.32 (dd, J = 10.5, 6.5 Hz, 2 H), 3.50 (s, 2 H),3.53 (dd, J = 10.5, 6.5 Hz, 2 H), 4.17 (br s, 2 H), 7.18-7.33 (m, 5 H). 13C NMR (DMSO-d6, 101 MHz): δ = 41.5, 57.4, 59.8, 60.5, 127.1, 128.5,128.8, 139.9.MS (CI): m/z = 222 ([M + H]+).
References:
Sokolenko, Yevhenii M.;Ostapchuk, Eugeniy N.;Artemenko, Artem;Grygorenko, Oleksandr O. [Synthesis,2017,vol. 49,# 14,p. 3112 - 3117]
7732-18-5
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607362-87-8
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179601-65-1
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93102-05-7
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