Trifluoroacetic acid → 3-(Hydroxymethyl)azetidine trifluoroacetate
Reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[OH:8][CH2:9][CH:10]1[CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11]1>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[OH:8][CH2:9][CH:10]1[CH2:13][NH:12][CH2:11]1Participants
3
Procedure
Trifluoroacetic acid (0.413 ml) was added to tert-butyl 3-(hydroxymethyl)azetidine-1-carboxylate (125 mg) with cooling in an ice bath, followed by stirring at the same temperature for 30 minutes. Then the reaction mixture was stirred at room temperature for 1.5 hours. The reaction mixture was concentrated to give a crude product of the title compound (209.8 mg) as a yellow oil.
Workup
- temperaturewith cooling in an ice bath
- stirringThen the reaction mixture was stirred at room temperature for 1.5 hours
- concentrationThe reaction mixture was concentrated
Sources & evidence
- ORD record
- ord-a3848cf7b5da400ea19765646c790181
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07790885B2
Reaction notes
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