Ammonia → 1-(Diphenylmethyl)-3-methylazetidin-3-amine

HRID 519210Notes

Reaction equation

HRID 519210 reaction equation
[CH:1]([N:14]1[CH2:17][C:16](OS(C)(=O)=O)([CH3:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:24]>C(Cl)Cl.CO>[CH:1]([N:14]1[CH2:17][C:16]([NH2:24])([CH3:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 100652951-Benzhydryl-3-methylazetidin-3-yl methanesulfonate

Product 1

HCID 100151051-(Diphenylmethyl)-3-methylazetidin-3-amineYield 58%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methanesulfonic acid 1-benzhydryl-3-methyl-azetidin-3-yl ester (12 g, 36.3 mmol) in DCM (100 mL) was added a saturated solution of ammonia in MeOH (200 mL) and the mixture was stirred for 3 h. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (eluting with 0-100% EtOAc in petroleum ether) to give 1-benzhydryl-3-methyl-azetidin-3-ylamine (5.31 g, 58%), which was used directly in step F. Alternatively, 1-benzhydryl-3-methyl-azetidin-3-ylamine can be prepared via steps D and E. TLC (eluting with 20% EtOAc/heptane) Rf=0.2.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by column chromatography on silica gel (eluting with 0-100% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-a9ef5f792b8047cd983b5ae03dec76b8
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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