Benzhydrylamine → HCID 18425412, compound

HRID 80845Notes

Reaction equation

HRID 80845 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH:7]([NH2:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[C@H:15](O)([C:21]([O-])=O)[C@@H:16]([OH:20])[C:17]([O-])=[O:18].[Na+].[K+].[OH-].[Na+]>C(Cl)Cl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH:7]([NH:14][CH:15]([CH3:21])[CH:16]([OH:20])[CH2:17][OH:18])([C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 7036BenzhydrylamineHCID 9357Potassium Sodium TartrateHCID 14798Sodium Hydroxide

Product 1

HCID 18425412HCID 18425412, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-(methyloxiran-2-yl)methanol (0.826 g, 9.38 mmol) in DCM was added α-aminodiphenylmethane (1.50 mL, 8.44 mmol) and titanium(IV) isopropoxide (5.5 mL, 18.7 mmol), and the reaction mixture was heated at 60° C. for 16 h. A saturated aqueous solution of Rochelle's salt was added to the mixture followed by a solution of 3 N NaOH. The reaction miture was stirred overnight. The aqueous phase was then extracted with DCM (3×). The combined organic layers were washed with brine, dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified via FCC (30-60% EtOAc/heptanes) to give the title compound. MS (ESI+) m/z 272.4 (M+H)+.

Workup

  1. extractionThe aqueous phase was then extracted with DCM (3×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified via FCC (30-60% EtOAc/heptanes)

Sources & evidence

ORD record
ord-ccb6c4fc81f643bb8cc751afb93159cb
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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