tert-Butyl 4-(3,3-difluoroazetidin-1-yl)piperidine-1-carboxylate → 4-(3,3-Difluoroazetidin-1-yl)piperidine

HRID 1945550Notes

Reaction equation

HRID 1945550 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:17][C:16]([F:19])([F:18])[CH2:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[F:19][C:16]1([F:18])[CH2:17][N:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH2:15]1

Participants

3

Reactant 1

HCID 59606191tert-Butyl 4-(3,3-difluoroazetidin-1-yl)piperidine-1-carboxylate

Product 1

HCID 596056804-(3,3-Difluoroazetidin-1-yl)piperidineYield 91%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A 25 mL round-bottomed flask was charged with a solution of 4-(3,3-difluoroazetidin-1-yl)piperidine-1-carboxylic acid tert-butyl ester (0.265 g, 0.96 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 4-(3,3-Difluoroazetidin-1-yl)piperidine as a white solid (0.154 g, 91%). 1H NMR (300 MHz, CDCl3): δ 3.54 (t, J=11.9 Hz, 4 H), 3.10 (dt, J=12.7, 3.9 Hz, 2 H), 2.59 (td, J=11.9, 2.6 Hz, 2 H), 2.24-2.13 (m, 1 H), 1.76-1.65 (m, 2 H), 1.30-1.15 (m, 2 H).

Workup

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

Sources & evidence

ORD record
ord-e66ac88851344967932febd4c920f621
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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