Trifluoroacetic acid → 3-Phenylazetidin-3-ol; trifluoroacetic acid

HRID 540389Notes

Reaction equation

HRID 540389 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[OH:8][C:9]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]1>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[OH:8][C:9]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:12][NH:11][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 65810524Tert-butyl 3-hydroxy-3-phenylazetidine-1-carboxylate

Product 1

HCID 669881473-Phenylazetidin-3-ol; trifluoroacetic acidYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 ml of trifluoroacetic acid is added to a solution containing 50 mg (0.19 mmol) of tert-butyl 3-hydroxy-3-phenylazetidine-1-carboxylate dissolved in 4 ml of dichloromethane. The reaction medium is stirred at ambient temperature for 3 hours and then concentrated. The crude product obtained is purified by silica gel chromatography (eluent 90/10 dichloromethane/methanol). 36 mg in the form of a white powder are obtained with a yield of 68%.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-b86cd5134ced443eaf9959beb2875b9e
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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