Trifluoroacetic acid → 4-(3-Azetidinyl)-2,2-dimethylmorpholine

HRID 1922650Notes

Reaction equation

HRID 1922650 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([N:12]2[CH2:17][CH2:16][O:15][C:14]([CH3:19])([CH3:18])[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[CH2:17][CH2:16][O:15][C:14]([CH3:19])([CH3:18])[CH2:13]2)[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 596059313-(2,2-Dimethylmorpholin-4-yl)azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 627847954-(3-Azetidinyl)-2,2-dimethylmorpholineYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(2,2-dimethylmorpholin-4-yl)azetidine-1-carboxylic acid tert-butyl ester (492 mg, 1.82 mmol) and TFA (5 mL) in DCM (10 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 4-Azetidin-3-yl-2,2-dimethylmorpholine as a white solid (302 mg, 97%). 1H NMR (CDCl3, 300 MHz): δ 3.73 (t, J=4.8 Hz, 2H); 3.64-3.51 (m, 4H); 3.18-3.11 (m, 1H); 2.23 (t, J=4.8 Hz, 2H); 2.23-2.07 (m, 1H); 2.06 (s, 2H); 1.25 (s, 6H).

Workup

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

Sources & evidence

ORD record
ord-dbfb81cb44ff4721956aa7678badaeb0
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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