Hydrochloric Acid → (S)-1-(4-(Difluoromethyl)benzyl)-3-hydroxypyrrolidin-2-one

HRID 1507271Notes

Reaction equation

HRID 1507271 reaction equation
Cl.O1CCOCC1.[Si]([O:15][C@H:16]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([CH:28]([F:30])[F:29])=[CH:24][CH:23]=2)[C:17]1=[O:31])(C(C)(C)C)(C)C>ClCCl>[F:30][CH:28]([F:29])[C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:18]2[CH2:19][CH2:20][C@H:16]([OH:15])[C:17]2=[O:31])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 123626683(S)-3-((tert-butyldimethylsilyl)oxy)-1-(4-(difluoromethyl)benzyl)pyrrolidin-2-one

Product 1

HCID 118207392(S)-1-(4-(Difluoromethyl)benzyl)-3-hydroxypyrrolidin-2-oneYield 123%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4 M HCl in dioxane (0.62 mL, 2.5 mmol) was added to a stirred solution of (S)-3-((tert-butyldimethylsilyl)oxy)-1-(4-(difluoromethyl)benzyl)pyrrolidin-2-one (440 mg, 1.24 mmol) in dichloromethane (1.24 mL) at RT. The reaction mixture was stirred for 2 h. The reaction mixture was concentrated in vacuo to afford (S)-1-(4-(difluoromethyl)benzyl)-3-hydroxypyrrolidin-2-one (368 mg, quantitative yield): LC-MS (M+H)+242.1.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-86e16c399de04813915d8515730b2ae3
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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