Lithium Hydroxide → {(5s,6s)-5-(Tert-butoxycarbonyl)-6-[(3-phenylpyrrolidin-1-yl)carbonyl]piperidin-3-yl}acetic acid

HRID 61430Notes

Reaction equation

HRID 61430 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][CH:5]1[CH2:10][NH:9][C@H:8]([C:11]([N:13]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:14]2)=[O:12])[C@@H:7]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:6]1.[OH-].[Li+]>C1COCC1>[C:27]([O:26][C:24]([C@@H:7]1[C@@H:8]([C:11]([N:13]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:14]2)=[O:12])[NH:9][CH2:10][CH:5]([CH2:4][C:3]([OH:31])=[O:2])[CH2:6]1)=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67304072tert-butyl(2S,3S)-5-(2-methoxy-2-oxoethyl)-2-[(3-phenylpyrrolidin-1-yl)carbonyl]piperidine-3-carboxylate

Product 1

HCID 67304514{(5s,6s)-5-(Tert-butoxycarbonyl)-6-[(3-phenylpyrrolidin-1-yl)carbonyl]piperidin-3-yl}acetic acidYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl(2S,3S)-5-(2-methoxy-2-oxoethyl)-2-[(3-phenylpyrrolidin-1-yl)carbonyl]piperidine-3-carboxylate in THF (3 mL) was cooled to 0° C. prior to the addition of lithium hydroxide (7 mg, 0.16 mmol). After warming to ambient temperature, the reaction mixture was stirred overnight. The volatiles were removed in-vacuo to afford 60 mg (87%) of {(5S,6S)-5-(tert-butoxycarbonyl)-6-[(3-phenylpyrrolidin-1-yl)carbonyl]piperidin-3-yl}acetic acid as an off-white solid that was used without neutralization and purification in the following coupling reaction. MS (ESI): 417 (M+H+).

Workup

  1. customThe volatiles were removed in-vacuo

Sources & evidence

ORD record
ord-aa3e50bc355b437c8ac95b525a845438
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Reaction notes

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