HCID 68905599, compound → HCID 55285612, compound

HRID 546474Notes

Reaction equation

HRID 546474 reaction equation
C(OC([NH:11][C@@H:12]1[CH2:17][CH2:16][C:15]([OH:19])([CH3:18])[CH2:14][C@@H:13]1[NH:20]C(OCC1C=CC=CC=1)=O)=O)C1C=CC=CC=1.[H][H]>[Pd].CO>[OH:19][C:15]1([CH3:18])[CH2:16][CH2:17][C@@H:12]([NH2:11])[C@@H:13]([NH2:20])[CH2:14]1

Participants

5

Reactant 2

HCID 68905599HCID 68905599, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 55285612HCID 55285612, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (350 mg) was suspended in a methanol solution (100 ml) of (1R*,2S*)-N1,N2-bis(benzyloxycarbonyl)-4-hydroxy-4-methyl-1,2-cyclohexanediamine (Stereoisomer A) (780 mg), and the suspension was stirred for 5 hours in a hydrogen atmosphere. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. After the residue was dissolved in dichloromethane (100 ml), and the solution was dried over anhydrous sodium sulfate, the solvent was distilled off to obtain the title compound (Stereoisomer A) (190 mg) as a colorless oil.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionAfter the residue was dissolved in dichloromethane (100 ml)
  4. dry with materialthe solution was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-67b2a64161e34a9e84df744fb9eaaa7a
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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