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

HRID 1507281Notes

Reaction equation

HRID 1507281 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]([Cl:28])=[CH:24][CH:23]=2)[C:17]1=[O:29])(C(C)(C)C)(C)C>ClCCl>[Cl:28][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:29])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 123669991(S)-3-((tert-butyldimethylsilyl)oxy)-1-(4-chlorobenzyl)pyrrolidin-2-one

Product 1

HCID 118207417(S)-1-(4-chlorobenzyl)-3-hydroxypyrrolidin-2-oneYield 102.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4 M HCl in dioxane (4.93 ml, 19.7 mmol) was added to a stirred solution of (S)-3-((tert-butyldimethylsilyl)oxy)-1-(4-chlorobenzyl)pyrrolidin-2-one (1.34 g, 3.94 mmol) in dichloromethane (4 mL) at RT. The reaction mixture was stirred for 2 h. The reaction mixture was concentrated in vacuo to afford (S)-1-(4-chlorobenzyl)-3-hydroxypyrrolidin-2-one (910 mg, 4.03 mmol, quantitative yield): LC-MS (M+H)+ 226.1; 1H NMR (500 MHz, methanol-d4) δ 7.37-7.33 (m, J=8.5 Hz, 2H), 7.27-7.23 (m, J=8.5 Hz, 2H), 4.52-4.37 (m, 2H), 4.34 (t, J=8.2 Hz, 1H), 3.30-3.18 (m, 2H), 1.84 (dq, J=12.8, 8.5 Hz, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-e53542a85c204b7883940bced636de08
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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