Water → (3S,4S)-1-Benzyl-4-(tert-butoxycarbonylamino-methyl)-pyrrolidine-3-carboxylic Acid

HRID 1163351Notes

Reaction equation

C([O:3][C:4]([C@H:6]1[C@@H:10]([CH2:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][N:8]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:7]1)=[O:5])C.O.[OH-].[Li+].O>C1COCC1>[CH2:20]([N:8]1[CH2:9][C@H:10]([CH2:11][NH:12][C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[C@H:6]([C:4]([OH:5])=[O:3])[CH2:7]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 2.9 (3R,4R) and (3S,4S)-1-benzyl-4-(tert-butoxycarbonylamino-methyl)-pyrrolidine-3-carboxylic acid ethyl ester (8.0 mmol) in 50 ml THF were added 671 mg lithium hydroxide mono hydrate (16 mmol) and 0.5 ml water. The solution was stirred at 40° C. and the reaction monitored by TLC. After 72 h the solvent was evaporated, the residue dissolved in dichloromethane, washed with water and brine, dried over Mg sulfate, filtered and evaporated. The residue was crystallized from a dichloromethane/hexane mixture.

Workup

customAfter 72 h the solvent was evaporated
dissolutionthe residue dissolved in dichloromethane
washwashed with water and brine
dry with materialdried over Mg sulfate
filtrationfiltered
customevaporated
customThe residue was crystallized from a dichloromethane/hexane mixture

Sources & evidence

ORD record: ord-1f9093fda89a4b25aa2a3cb7fca49b8c
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820823B2

Reaction notes

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