Methanol → HCID 15434420, compound

HRID 1473006Notes

Reaction equation

HRID 1473006 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([O-])=[O:14])=[CH:11][C:10]=1[CH:18]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:19][CH2:20][N:21]([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COCCO[AlH2-]OCCOC.[Na+].CO.O>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([CH2:13][OH:14])=[CH:11][C:10]=1[C@@H:18]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH2:19][CH2:20][N:21]([CH:22]([CH3:23])[CH3:24])[CH:25]([CH3:26])[CH3:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 16684438Red-AlHCID 86691364HCID 86691364, compound

Product 1

HCID 15434420HCID 15434420, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

5 gm (R)-[4-benzyloxy-3-(3-diisopropylamino-1-phenyl propyl)benzoate and 25 ml toluene was added under nitrogen atmosphere to a solution of 5.5 g Vitride in 50 ml toluene at 0° C. to 5° C. After stirring at room temperature for 5 hours, methanol was added drop wise at 0° C. to 5° C. After raising the temperature to room temperature, water and toluene was added and stirred for 30 minutes at 25° C. to 35° C. Layers were separated. Toluene layer after complete distillation afforded the title compound as (R)-[4-benzyloxy-3-(3-diisopropylamino-1-phenyl propyl)-phenyl]-methanol of formula (H).

Workup

  1. temperatureAfter raising the temperature to room temperature
  2. stirringstirred for 30 minutes at 25° C. to 35° C
  3. customLayers were separated
  4. distillationToluene layer after complete distillation

Sources & evidence

ORD record
ord-09de82c397444aa585c51deb01498755
Source dataset
uspto-grants-2015_04
Patent number
US09012678B2

Reaction notes

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