Benzhydrylamine → HCID 14852479, compound

HRID 1051679Notes

Reaction equation

HRID 1051679 reaction equation
Br[CH2:2][CH:3]1[CH:5]([CH3:6])[O:4]1.[C:7]1([CH:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[NH2:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CO>[CH:13]([N:14]1[CH2:2][CH:3]([OH:4])[CH:5]1[CH3:6])([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 7036BenzhydrylamineHCID 127416282-(Bromomethyl)-3-methyloxirane

Product 1

HCID 14852479HCID 14852479, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A 500-mL round-bottom flask was charged with 2-(bromomethyl)-3-methyloxirane (42.4 g, 280 mmol), methanol (120 mL), and diphenylmethanamine (44 mL, 260 mmol), and the resulting solution stirred overnight at 80° C. The reaction mixture was cooled to room temperature and concentrated. The residue was purified via column chromatography on silica gel (eluting with 50:1, dichloromethane/methanol) to afford 1-benzhydryl-2-methylazetidin-3-ol (25 g, 35%) as a white solid. MS (ESI, pos. ion) m/z 254 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was purified via column chromatography on silica gel (eluting with 50:1, dichloromethane/methanol)

Sources & evidence

ORD record
ord-583768c40a744d3282965990aa6fb5ef
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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