HCID 130980049, compound → HCID 131026831, compound

HRID 2208147Notes

Reaction equation

HRID 2208147 reaction equation
C([O:8][C@@H:9]1[CH2:14][CH2:13][C@@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:11][C@@H:10]1[CH3:23])C1C=CC=CC=1>CO.[Pd]>[OH:8][C@H:9]1[CH2:14][CH2:13][C@@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])[CH2:11][C@H:10]1[CH3:23]

Participants

4

Reactant 1

HCID 130980049HCID 130980049, compound

Product 1

HCID 131026831HCID 131026831, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl [(1R*,3S*,4R*)-4-(benzyloxy)-3-methylcyclohexyl]carbamate (example C7; 14.0 g; 43.8 mmol) dissolved in MeOH (440 mL) is pressure hydrogenated over Pd (10% on charcoal; 1.4 g) at 50 bar and ambient temperature for 72 hours. The catalyst is removed by filtration through a pad of celite. The filtrate is concentrated under reduced pressure. The residue is chromatographed on silica gel (cyclohexane/AcOEt—70:30 to 50:50) to yield 8.5 g of the tile compound as colourless oil.

Workup

  1. customThe catalyst is removed by filtration through a pad of celite
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. customThe residue is chromatographed on silica gel (cyclohexane/AcOEt—70:30 to 50:50)

Sources & evidence

ORD record
ord-fdd7deaf64e24e2d8d7e432f6fcfa22e
Source dataset
uspto-grants-2016_06
Patent number
US09376442B2

Reaction notes

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