HCID 178484124, compound → HCID 178484119, compound

HRID 967165Notes

Reaction equation

HRID 967165 reaction equation
[C:1]([O:5][C:6](=[O:29])[N:7]([CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21]CC2C=CC=CC=2)[CH2:12][CH2:11]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:29])[N:7]([CH2:9][C@H:10]1[CH2:11][CH2:12][C@H:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21])[CH2:14][CH2:15]1)[CH3:8])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 178484124HCID 178484124, compound

Product 1

HCID 178484119HCID 178484119, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.15 g (5.3 mmol) of trans-[4-(4-benzyloxy-butoxy)-cyclohexylmethyl]-methyl-carbamic acid tert-butyl ester were dissolved in 20.0 ml of methanol, 0.3 g palladium on charcoal (10%) were added and the reaction mixture hydrogenated at normal pressure until the consumption of hydrogen came to an end. Then, it was filtered over celite and evaporated giving 1.60 g (95.6%) of trans-[4-(4-hydroxy-butoxy)-cyclohexylmethyl]-methyl-carbamic acid tert-butyl ester as colorless viscous oil, MS: 315 (M+).

Workup

  1. customthe reaction mixture hydrogenated at normal pressure until the consumption of hydrogen
  2. filtrationThen, it was filtered over celite
  3. customevaporated

Sources & evidence

ORD record
ord-80f7de46ec7048049b7471884f12dc6c
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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