Hydrochloric Acid → (S)-3-amino-1-(2-hydroxyethyl)pyrrolidin-2-one hydrochloride

HRID 912457Notes

Reaction equation

HRID 912457 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[CH2:15][CH2:14][C@H:13]([NH:16]C(=O)OC(C)(C)C)[C:12]1=[O:24])(C(C)(C)C)(C)C.O1CCOCC1.[ClH:31]>>[ClH:31].[NH2:16][C@H:13]1[CH2:14][CH2:15][N:11]([CH2:10][CH2:9][OH:8])[C:12]1=[O:24]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57736552(S)-tert-butyl 1-(2-(tert-butyldimethylsilyloxy)ethyl)-2-oxopyrrolidin-3-ylcarbamate

Product 1

HCID 67416985(S)-3-amino-1-(2-hydroxyethyl)pyrrolidin-2-one hydrochlorideYield 100%

Procedure

(S)-tert-Butyl 1-(2-(tert-butyldimethylsilyloxy)ethyl)-2-oxopyrrolidin-3-ylcarbamate prepared according to Example 11; 200 mg, 0.558 mmol) was dissolved in 4M hydrogen chloride in dioxane (2.8 mL, 11.2 mmol), and the reaction mixture was allowed to stir at ambient temperature overnight. The reaction mixture was concentrated to yield (S)-3-amino-1-(2-hydroxyethyl)pyrrolidin-2-one hydrochloride (101 mg, 100%) which was taken on to the next step without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-4e49b98176054d4992133a1302547f2f
Source dataset
uspto-grants-2011_09
Patent number
US08026233B2

Reaction notes

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