Cyclohexanone → HCID 68715687, compound

HRID 1911515Notes

Reaction equation

HRID 1911515 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[C:21]1(=O)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.[BH3-]C#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH3:1][O:2][C:3](=[O:20])[CH:4]([NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:14]=1

Participants

6

Reactant 3

HCID 7967CyclohexanoneHCID 5003444Sodium cyanoborohydrideHCID 22980961HCID 22980961, compound

Product 1

HCID 68715687HCID 68715687, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of (3-amino-phenyl)-tert-butoxycarbonylamino-acetic acid methyl ester (165 mg, CAS 180081-34-9) in MeOH (5 ml) was treated under an argon atmosphere with cyclohexanone (0.07 ml), zinc chloride (321 mg) and NaBH3CN (111 mg) and stirred overnight at 40° C. The MeOH was distilled off. The residue was taken up in EtOAc and H2O. The aqueous phase was back extracted with EtOAc. The combined organics were washed with water, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient: cyclohexane ->cyclohexane/EtOAc 14:1) to give (RS)-tert-butoxycarbonylamino-(3-cyclohexylamino-phenyl)-acetic acid methyl ester (200 mg, 94%) as viscous colorless oil.

Workup

  1. distillationThe MeOH was distilled off
  2. extractionThe aqueous phase was back extracted with EtOAc
  3. washThe combined organics were washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (silica gel; gradient: cyclohexane ->cyclohexane/EtOAc 14:1)

Sources & evidence

ORD record
ord-2db2946dfd2048849758d1bad46bd9a1
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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