Lithium Hydroxide → (4R)-1-Boc-4-(methylsulfonyl)-L-proline

HRID 1697698Notes

Reaction equation

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

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 667719431-tert-Butyl 2-methyl (2S,4R)-4-methanesulfonylpyrrolidine-1,2-dicarboxylate

Product 1

HCID 18446444(4R)-1-Boc-4-(methylsulfonyl)-L-proline

Procedure

In analogy to the procedure described in example 253e, (2S,4R)-4-methanesulfonyl-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 yellow solid. MS (ESI): m/z=294.2 [M+H]+.

Sources & evidence

ORD record: ord-5341708094684c59a4931ffb673a7210
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163793B2

Reaction notes

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