Trifluoroacetic acid → 3-Pentoxy-3-phenylazetidine trifluoroacetate

HRID 540375Notes

Reaction equation

HRID 540375 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:8]([O:13][C:14]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]1)[CH2:9][CH2:10][CH2:11][CH3:12]>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:8]([O:13][C:14]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:17][NH:16][CH2:15]1)[CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 669885513-Pentoxy-3-phenyl-1-(tert-butoxycarbonyl)azetidine

Product 1

HCID 669889253-Pentoxy-3-phenylazetidine trifluoroacetateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.5 ml of trifluoroacetic acid are added to a solution containing 3.34 g (10 mmol) of 3-pentoxy-3-phenyl-1-(tert-butoxycarbonyl)azetidine dissolved in 10 ml of dichloromethane. The reaction medium is stirred at ambient temperature for 2 hours 30 min and then concentrated. The crude product obtained is purified by silica gel chromatography (eluent 90/10 dichloromethane/methanol). 3.5 g in the form of a pale yellow oil are obtained with a yield of 100%.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-6926ba8cc6ed4f37a899bfd8a31ed63a
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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