Water → (1R,2E)-2-hydroxyimino-1,2-diphenylethanol;trans-(1R,2R)-cyclohexane-1,2-diamine

HRID 1721505Notes

Reaction equation

HRID 1721505 reaction equation
[C@@H:1]1([NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]1[NH2:7].O.[OH:10][CH:11]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:12](=[N:19][OH:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1C=CC=CC=1>[C@@H:1]1([NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]1[NH2:7].[OH:10][C@H:11]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)/[C:12](=[N:19]/[OH:20])/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9924(+-)-Benzoin oximeHCID 438061,2-Diaminocyclohexane, trans-

Product 1

HCID 88417869(1R,2E)-2-hydroxyimino-1,2-diphenylethanol;trans-(1R,2R)-cyclohexane-1,2-diamine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2.00 g (17.5 mmol) of (1R,2R)-(-)-1,2-cyclohexanediamine of α!D20 =-36.7° (c 4.14, H2O) and 4.00 g (17.6 mmol) of dl-1-hydroxy-2-hydroxyimino-1,2-diphenylethane were added to 10 ml of benzene and then heated and stirred, and the solution was cooled to room temperature. Afterward, the precipitated crystals were collected by filtration and then recrystallized from 30 ml of benzene twice to obtain 2.30 g of (1R,2R)-(-)-1,2-cyclohexanediamine·(R)-(-)-(E)-1-hydroxy-2-hydroxyimino-1,2-diphenylethane. Physical properties of the product are as follows.

Workup

  1. temperatureheated
  2. filtrationAfterward, the precipitated crystals were collected by filtration
  3. customrecrystallized from 30 ml of benzene twice

Sources & evidence

ORD record
ord-7ddafd4ef86d43d394d657817c8bf3e6
Source dataset
uspto-grants-1996_04
Patent number
US05510520

Reaction notes

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