Water → HCID 70357593, compound

HRID 1165833Notes

Reaction equation

HRID 1165833 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:23][CH2:22][C@@:12]34[C:13]5[CH:14]=[C:15]([O:20][CH3:21])[CH:16]=[CH:17][C:18]=5[CH2:19][C@@H:6]2[C@:7]3([CH2:25][CH3:26])[CH2:8][CH2:9][C:10](=[O:24])[CH2:11]4)[CH2:3][CH2:2]1.[BH4-].[Na+].O>C(O)C>[CH:1]1([CH2:4][N:5]2[CH2:23][CH2:22][C@@:12]34[C:13]5[CH:14]=[C:15]([O:20][CH3:21])[CH:16]=[CH:17][C:18]=5[CH2:19][C@@H:6]2[C@:7]3([CH2:25][CH3:26])[CH2:8][CH2:9][C@H:10]([OH:24])[CH2:11]4)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 70357633HCID 70357633, compound

Product 1

HCID 70357593HCID 70357593, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.95 g (2.7 mMol) of N-cyclopropylmethyl-14β-ethyl-3-methoxymorphinan-6-one (starting compound of example 11a) are dissolved in 70 ml of ethanol, then 0.53 g of NaBH4 (0.14 mol) are added, and the mixture stirred for 3 hours at room temperature. The reaction mixture is stopped with 20 ml of water and subsequent stirring for 30 minutes. The ethanol is distilled off and the residue is extracted three times with methylene chloride. After drying and concentrating, the organic phase yields a colorless oil, which is separated by chromatography on silica gel (methylene chloride/methanol/conc. ammonia 99:1:0.1) into the two compounds named in the title. Both compounds are isolated as colorless oils.

Workup

  1. stirringsubsequent stirring for 30 minutes
  2. distillationThe ethanol is distilled off
  3. extractionthe residue is extracted three times with methylene chloride
  4. customAfter drying
  5. concentrationconcentrating
  6. customthe organic phase yields a colorless oil, which
  7. customis separated by chromatography on silica gel (methylene chloride/methanol/conc. ammonia 99:1:0.1) into the two compounds
  8. customBoth compounds are isolated as colorless oils

Sources & evidence

ORD record
ord-45b43d78b4ec4cd5acc05858e4f81b20
Source dataset
uspto-grants-1990_03
Patent number
US04912114

Reaction notes

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