tert-Butyl 3-(4-fluoro-1-piperidyl)azetidine-1-carboxylate → 1-(Azetidin-3-yl)-4-fluoropiperidine

HRID 1922671Notes

Reaction equation

HRID 1922671 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([N:12]2[CH2:17][CH2:16][CH:15]([F:18])[CH2:14][CH2:13]2)[CH2:9]1)=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH:8]1[CH2:11][CH:10]([N:12]2[CH2:17][CH2:16][CH:15]([F:18])[CH2:14][CH2:13]2)[CH2:9]1

Participants

3

Reactant 1

HCID 59605431tert-Butyl 3-(4-fluoro-1-piperidyl)azetidine-1-carboxylate

Product 1

HCID 110948981-(Azetidin-3-yl)-4-fluoropiperidineYield 74%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A 25 mL round-bottomed flask was charged with a solution of 3-(4-fluoro-piperidin-1-yl)-azetidine-1-carboxylic acid tert-butyl ester (0.59 g, 2.26 mmol) in DCM/TFA (4 mL/4 mL). The reaction mixture was stirred for 6 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 1-Azetidin-3-yl-4-fluoropiperidine as a pale yellow oil (0.263 g, 74%). 1H NMR (CDCl3, 400 MHz) δ 4.60 (m, 1H); 3.64-3.52 (m, 4H); 3.26-3.18 (m, 1H); 2.45-2.38 (m, 2H); 2.28-2.17 (m, 2H); 1.96-1.81 (m, 4H)

Workup

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

Sources & evidence

ORD record
ord-432738fb37114769a48311130208ab4a
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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