Water → HCID 67704038, compound

HRID 1941354Notes

Reaction equation

HRID 1941354 reaction equation
[NH2:1][CH:2]([CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[CH:3]([OH:16])[CH2:4][CH:5]([CH:13]([CH3:15])[CH3:14])[C:6]([NH:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[O:7].[CH3:24][CH:25]1[CH2:30][CH2:29][C:28](=O)[CH2:27][CH2:26]1.[BH4-].[Na+].O>C1C=CC=CC=1.CCO>[NH4+:1].[OH-:7].[OH:16][CH:3]([CH:2]([NH:1][CH:28]1[CH2:29][CH2:30][CH:25]([CH3:24])[CH2:26][CH2:27]1)[CH2:17][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)[CH2:4][CH:5]([CH:13]([CH3:14])[CH3:15])[C:6]([NH:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[O:7]

Participants

8

Reactant 4

HCID 962WaterHCID 115254-MethylcyclohexanoneHCID 4311764Sodium borohydrideHCID 67703993HCID 67703993, compound

Product 2

HCID 14923Ammonium HydroxideHCID 67704038HCID 67704038, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

[αR(αR*,γR*,δS*)]-δ-Amino-γ-hydroxy-α-(1-methylethyl)-N-(2-methylpropyl)cyclohexanehexanamide (50 mg, 0.153 mmol) and 4-methylcyclohexanone (19 mg, 0.169 mmol) were dissolved in benzene (10 mL). Ti(iPrO)4 (65 mg, 0.23 mmol) was added and the mixture was refluxed under N2 for 24 h. The mixture was cooled, diluted with 10 mL of EtOH and NaBH4 (12 mg, 0.307 mmol) was added. The mixture was then heated at reflux for 10 h. Water (1 mL) was added and the solvents were removed in vacuo. The residue was dissolved with CH2Cl2, and sequentially washed with dil. Na2CO3 and brine. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. Silica gel chromatography (1:0:0 to 9:1:0.1 CH2Cl2 :MeOH:NH4OH gradient) of the concentrate afforded the title compound (19 mg, 29%), mp 119° C.

Workup

  1. temperaturethe mixture was refluxed under N2 for 24 h
  2. temperatureThe mixture was cooled
  3. additionwas added
  4. temperatureThe mixture was then heated
  5. temperatureat reflux for 10 h
  6. customthe solvents were removed in vacuo
  7. dissolutionThe residue was dissolved with CH2Cl2
  8. washsequentially washed with dil. Na2CO3 and brine
  9. dry with materialThe organic phase was dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c66517088c4b49cfa20370453ce9655d
Source dataset
uspto-grants-1997_12
Patent number
US05703129

Reaction notes

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