[(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxy-7-methyl-oct-6-enyl]carbamic acid tert-butyl ester → [(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxy-7-methyl-octyl]carbamic acid tert-butyl ester

HRID 1373098Notes

Reaction equation

HRID 1373098 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C@@H:8]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C@@H:9]([OH:27])[CH2:10][C@H:11]([C:17](=[O:26])[NH:18][CH:19]1[CH2:24][CH:23]2[CH2:25][CH:20]1[CH2:21][CH2:22]2)[CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:35])[NH:7][C@@H:8]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C@@H:9]([OH:27])[CH2:10][C@H:11]([C:17](=[O:26])[NH:18][CH:19]1[CH2:24][CH:23]2[CH2:25][CH:20]1[CH2:21][CH2:22]2)[CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 69507684[(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxy-7-methyl-oct-6-enyl]carbamic acid tert-butyl ester

Product 1

HCID 69508375[(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxy-7-methyl-octyl]carbamic acid tert-butyl esterYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

[(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxy-7-methyl-oct-6-enyl]-carbamic acid tert-butyl ester (D6) (1.61 g, 3.33 mmol) in methanol (30 ml) was hydrogenated over 10% Pd/C (300 mg) for 3.75 h. The catalyst was filtered and the filtrate evaporated to afford D7 (93%).

Workup

  1. filtrationThe catalyst was filtered
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-013efa6b7b37405996e5fce39f55b4b6
Source dataset
uspto-grants-2007_01
Patent number
US07160905B2

Reaction notes

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