Hydrogen chloride-ethyl acetate → (1R,2R)-1-amino-1-(3,4,5-trifluorophenyl)propan-2-ol hydrochloride

HRID 16326

Reaction equation

HRID 16326 reaction equation
C(OC(=O)C)C.[ClH:7].C(OC(=O)[NH:14][C@H:15]([C:19]1[CH:24]=[C:23]([F:25])[C:22]([F:26])=[C:21]([F:27])[CH:20]=1)[C@H:16]([OH:18])[CH3:17])(C)(C)C>C(OCC)(=O)C>[ClH:7].[NH2:14][C@H:15]([C:19]1[CH:20]=[C:21]([F:27])[C:22]([F:26])=[C:23]([F:25])[CH:24]=1)[C@H:16]([OH:18])[CH3:17]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 68717986tert-butyl [(1R,2R)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]carbamate

Product 1

HCID 68718335(1R,2R)-1-amino-1-(3,4,5-trifluorophenyl)propan-2-ol hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 4 N hydrochloric acid ethyl acetate solution (20 mL) was added to an ethyl acetate solution (50 mL) of [(1R,2R)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]carbamic acid tert-butyl ester (4.49 g). This reaction solution was stirred at room temperature for 5 hr. The reaction solution was concentrated under reduced pressure to give 3.5 g of the title compound. The physical property values of this compound were as follows:

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fa59c57344bc4b0684a86df029dac512
Source dataset
uspto-grants-2010_06
Patent number
US07737141B2

Linked notes

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