5-(Hydroxymethyl)pyrrolidin-2-one → (4S)-4-cyclohexyl-L-proline

HRID 280381Notes

Reaction equation

HRID 280381 reaction equation
[OH:1]CC1NC(=O)CC1.[CH:9]1([C@H:15]2[CH2:19][NH:18][C@H:17]([CH2:20][OH:21])[CH2:16]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C1([C@@H]2N3C(=O)CCC3CO2)C=CC=CC=1>>[CH:9]1([C@H:15]2[CH2:19][NH:18][C@H:17]([C:20]([OH:1])=[O:21])[CH2:16]2)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

4

Reactant 3

HCID 5583595-(Hydroxymethyl)pyrrolidin-2-oneHCID 13573803(R)-Tetrahydro-3-phenyl-3H,5H-pyrrolo[1,2-c]oxazol-5-oneHCID 13648259(2S-trans)-4-cyclohexyl-2-pyrrolidinemethanol

Product 1

HCID 9815559(4S)-4-cyclohexyl-L-proline

Procedure

(trans)-4-Cyclohexyl-L-proline was prepared from 5-hydroxymethyl-2-pyrrolidone using the procedure described in Example 1, but substituting the following methodology for preparing (2S-trans)-4-cyclohexyl-2-pyrrolidinemethanol from (R)-tetrahydro-3-phenyl-3H,5H-pyrrolo[1,2-c]oxazol-5-one:

Sources & evidence

ORD record
ord-8973e0a2498e4129a041fd5f98359b23
Source dataset
uspto-grants-1986_05
Patent number
US04588819

Reaction notes

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