[1,3′-Biazetidine]-1′-carboxylic acid, 3,3-difluoro-, 1,1-dimethylethyl ester → 3,3-Difluoro-1,3′-biazetidine

HRID 1945548Notes

Reaction equation

HRID 1945548 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([N:12]2[CH2:15][C:14]([F:17])([F:16])[CH2:13]2)[CH2:9]1)=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[F:16][C:14]1([F:17])[CH2:15][N:12]([CH:10]2[CH2:11][NH:8][CH2:9]2)[CH2:13]1

Participants

3

Reactant 1

HCID 59606024[1,3′-Biazetidine]-1′-carboxylic acid, 3,3-difluoro-, 1,1-dimethylethyl ester

Product 1

HCID 596054253,3-Difluoro-1,3′-biazetidineYield 37%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A 10 mL round-bottomed flask was charged with a solution of 3,3-difluoro-[1,3′]biazetidinyl-1′-carboxylic acid tert-butyl ester (0.15 g, 0.61 mmol) in DCM/TFA (3 mL/3 mL). The reaction mixture was stirred for 3 h at room temperature. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the desired product was eluted using 2 M NH3 in MeOH to give 3,3-Difluoro-[1,3′]biazetidinyl as a colourless oil (0.033 g, 37%). 1H NMR (300 MHz, CDCl3): δ 3.73-3.55 (m, 8 H), 3.57-3.43 (m, 1 H), 2.77 (s, 1 H)

Workup

  1. washThe cartridge was washed with MeOH
  2. washthe desired product was eluted

Sources & evidence

ORD record
ord-4d3107dae92f4ebcac0fd2f84c83c1d1
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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