Trifluoroacetic acid → 3-(Hydroxymethyl)azetidine trifluoroacetate
Reaction equation
[OH:1][CH2:2][CH:3]1[CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4]1.[F:14][C:15]([F:20])([F:19])[C:16]([OH:18])=[O:17]>>[F:14][C:15]([F:20])([F:19])[C:16]([OH:18])=[O:17].[OH:1][CH2:2][CH:3]1[CH2:6][NH:5][CH2:4]1Participants
3
Procedure
To tert-butyl 3-(hydroxymethyl)azetidine-1-carboxylate (125 mg) was added trifluoroacetic acid (0.413 ml) while cooling in an ice bath, followed by stirring at the same temperature for 30 min. Then, the reaction mixture was stirred at room temperature for 1.5 hr. The reaction mixture was concentrated to provide a crude product of the titled compound as a yellow oil (209.8 mg).
Workup
- temperaturewhile cooling in an ice bath
- stirringThen, the reaction mixture was stirred at room temperature for 1.5 hr
- concentrationThe reaction mixture was concentrated
Sources & evidence
- ORD record
- ord-f55fba82ad1e4096990f4d9d723f1410
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08288538B2
Reaction notes
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