Hydrochloric Acid → (S)-1-(3-aminopyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone mono hydrochloride

HRID 1666670Notes

Reaction equation

HRID 1666670 reaction equation
[F:1][C:2]([F:27])([F:26])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([N:13]2[CH2:17][CH2:16][C@H:15]([NH:18]C(=O)OC(C)(C)C)[CH2:14]2)=[O:12])=[CH:6][CH:5]=1.[ClH:28]>C(OCC)(=O)C>[ClH:28].[NH2:18][C@H:15]1[CH2:16][CH2:17][N:13]([C:11](=[O:12])[CH2:10][C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:26])[F:27])=[CH:9][CH:8]=2)[CH2:14]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57970134HCID 57970134, compound

Product 1

HCID 86636479(S)-1-(3-aminopyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone mono hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

t-Butyl ((S)-1-(2-(4-trifluoromethoxyphenyl)ethanoyl)pyrrolidin-3-yl)carbamate (144 g) was suspended in ethyl acetate (300 mL), followed by addition of a solution (278 mL) of 4 M HCl in ethyl acetate, and the mixture was stirred at room temperature for 3 days. The precipitated solids were collected by filtration to obtain the title compound (67 g). The filtrate was concentrated under reduced pressure, followed by addition of hexane and diisopropyl ether, and the precipitated solids were collected by filtration to obtain the title compound (52 g).

Workup

  1. filtrationThe precipitated solids were collected by filtration

Sources & evidence

ORD record
ord-9f28aa9428f443cc8c5234c9f5959bbb
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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