Trifluoroacetic acid → 1-(Azetidin-3-yl)-3,3-difluoropyrrolidine

HRID 1922696Notes

Reaction equation

HRID 1922696 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([N:12]2[CH2:16][CH2:15][C:14]([F:18])([F:17])[CH2:13]2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:11][CH:10]([N:12]2[CH2:16][CH2:15][C:14]([F:17])([F:18])[CH2:13]2)[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59605561Tert-butyl 3-(3,3-difluoropyrrolidin-1-yl)azetidine-1-carboxylate

Product 1

HCID 596053851-(Azetidin-3-yl)-3,3-difluoropyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(3,3-difluoropyrrolidin-1-yl)azetidine-1-carboxylic acid tert-butyl ester (193 mg, 0.74 mmol) and TFA (1 mL) in DCM (2 mL) was stirred at room temperature for 2 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge, washed with MeOH/DCM and eluted with 2M NH3/MeOH affording 1-Azetidin-3-yl-3,3-difluoropyrrolidine as a white solid (122 mg, quant.). 1H NMR (CDCl3, 300 MHz): δ 3.63 (m, 4H), 3.48 (m, 1H), 2.87 (t, J=13.1 Hz, 2H), 2.70 (t, J=7.0 Hz, 2H) and 2.29 (m, 2H)

Workup

  1. washwashed with MeOH/DCM
  2. washeluted with 2M NH3/MeOH

Sources & evidence

ORD record
ord-935b28a814e5429c93e45ce762163297
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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