Benzhydrylamine → HCID 18425456, compound

HRID 1280555Notes

Reaction equation

HRID 1280555 reaction equation
[CH3:1][C:2]1([CH3:7])[O:4][CH:3]1[CH2:5][OH:6].[NH2:8][CH:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[Na+]>ClCCl.[Cl-].[Na+].O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH:9]([NH:8][C:2]([CH3:7])([CH3:1])[CH:3]([OH:4])[CH2:5][OH:6])([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 7036BenzhydrylamineHCID 14798Sodium HydroxideHCID 167724(3,3-Dimethyloxiran-2-yl)methanol

Product 1

HCID 18425456HCID 18425456, compoundYield 18.2%

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 6344DichloromethaneSolvent3×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of (3,3-dimethyloxiranyl)methanol (10 g, 98 mmol) in dichloromethane (735 mL) was combined with a solution of titanium isopropoxide (50mL, 169.4mmol) in dichloromethane (100 mL) and a solution of aminodiphenyl-methane (40.6 mL, 235 mmol) in dichloromethane (100 mL), and the reaction mixture was stirred at room temperature for 48 hours. A solution of 10% sodium hydroxide in brine was added and the suspension stirred for an additional 12 hours, filtered and washed with 0.2M hydrochloric acid. The layers were separated, and the organic layer was dried over magnesium sulfate, filtered, concentrated. The residue was purified by column chromatography using 4:1 hexane/ethyl acetate as eluant to give 5.1 g of 3-(benzhydryl-amino)-3-methylbutane-1,2-diol.

Workup

  1. filtrationfiltered
  2. washwashed with 0.2M hydrochloric acid
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c5f12105c2d34d2d893ca3d05135904c
Source dataset
uspto-grants-2002_09
Patent number
US06451804B1

Reaction notes

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