Trifluoroacetic acid methylene chloride → 3-(fluoromethyl)azetidine, trifluoroacetic acid

HRID 717500Notes

Reaction equation

HRID 717500 reaction equation
[F: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].C(Cl)Cl>>[F:14][C:15]([F:20])([F:19])[C:16]([OH:18])=[O:17].[F:1][CH2:2][CH:3]1[CH2:6][NH:5][CH2:4]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 768501961-Azetidinecarboxylic acid, 3-(fluoromethyl)-, 1,1-dimethylethyl ester

Product 1

HCID 896201983-(fluoromethyl)azetidine, trifluoroacetic acid

Procedure

tert-Butyl 3-(fluoromethyl)azetidine-1-carboxylate (0.1 g, 0.53 mmol) and trifluoroacetic acid/DCM (1:1, 5.3 mL) was stir at room temperature for 30 min. Then the reaction mixture was concentrated on a rotary evaporator to afford 3-(fluoromethyl)azetidine 2,2,2-trifluoroacetate as clear oil. 1H NMR (DMSO-d6; TFA salt): δ 8.74 (br, 2H), 4.54 (dd, 2H), 4.08-3.98 (m, 2H), 3.84-3.76 (m, 2H), 3.20-3.06 (m, 1H).

Workup

  1. concentrationThen the reaction mixture was concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-a23c216254074f11a314e3874c5275c6
Source dataset
uspto-grants-2015_11
Patent number
US09193714B2

Reaction notes

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