Ammonium formate → 2(S)-amino-1-cyclohexyl-3(S)-hydroxy-6-methylheptane

HRID 259832Notes

Reaction equation

HRID 259832 reaction equation
C([N:8]([C@H:16]([C@@H:24]([OH:30])[CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)CC1C=CC=CC=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[C].[Pd]>[NH2:8][C@H:16]([C@@H:24]([OH:30])[CH2:25][CH2:26][CH:27]([CH3:28])[CH3:29])[CH2:17][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 543040652(S)-(N,N-Dibenzylamino)-1-cyclohexyl-3(S)-hydroxy-6-methylheptane

Product 1

HCID 146717222(S)-amino-1-cyclohexyl-3(S)-hydroxy-6-methylheptaneYield 148.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2(S)-(N,N-Dibenzylamino)-1-cyclohexyl-3(S)-hydroxy-6-methylheptane (5 g) was dissolved in methanol (50 ml). Ammonium formate (6.18 g) and then 10% palladium-carbon (50% wet, 0.5 g) were added thereto, and the mixture was vigorously stirred at room temperature. After the completion of the reaction, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. Ethyl acetate and water were added to the concentrated residue for extraction. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 4.13 g of 2(S)-amino-1-cyclohexyl-3(S)-hydroxy-6-methylheptane.

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionEthyl acetate and water were added to the concentrated residue for extraction
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-fd8dddd55e1c422eb61b0cff155d2803
Source dataset
uspto-grants-1996_06
Patent number
US05523410

Reaction notes

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