Lithium Hydroxide → (2S,4R)-4-Cyclopropylmethanesulfonyl-pyrrolidine-1,2-dicarboxylic Acid 1-tert-butyl Ester

HRID 1697710Notes

Reaction equation

C[O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([CH2:13][CH:14]2[CH2:16][CH2:15]2)(=[O:12])=[O:11])[CH2:7][N:6]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:4].[OH-].[Li+]>>[C:20]([O:19][C:17]([N:6]1[CH2:7][C@H:8]([S:10]([CH2:13][CH:14]2[CH2:15][CH2:16]2)(=[O:12])=[O:11])[CH2:9][C@H:5]1[C:3]([OH:4])=[O:2])=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 66771843(2S,4R)-4-cyclopropylmethanesulfonyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Product 1

HCID 66772266(2S,4R)-4-Cyclopropylmethanesulfonyl-pyrrolidine-1,2-dicarboxylic Acid 1-tert-butyl Ester

Procedure

In analogy to the procedure described in example 253e, (2S,4R)-4-cyclopropylmethanesulfonyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester was saponified in the presence of lithium hydroxide to give the title compound as white solid. MS (ESI): m/z=333.6 [M+H]+.

Sources & evidence

ORD record: ord-fbc2d202e3a7403a832fd4542e1f2b4d
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163793B2

Reaction notes

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