HCID 178484035, compound → HCID 178484032, compound

HRID 967143Notes

Reaction equation

HRID 967143 reaction equation
C(O[C:9](=O)[N:10]([CH2:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([CH2:19][CH2:20][OH:21])[CH2:15][CH2:14]1)C)C1C=CC=CC=1>O1CCCC1.[Pd]>[CH3:9][NH:10][CH2:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([CH2:19][CH2:20][OH:21])[CH2:15][CH2:14]1

Participants

4

Reactant 1

HCID 178484035HCID 178484035, compound

Product 1

HCID 178484032HCID 178484032, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

0.62 g (2.03 mmol) trans-[4-(2-hydroxy-ethyl)-cyclohexylmethyl]-methyl-carbamic acid benzyl ester dissolved in 10 ml of tetrahydrofuran were submitted to a hydrogenation over 0.3 g of 5% palladium on charcoal as catalyst, at normal pressure and ambient temperature. The cleavage of the benzyloxycarbonyl group was complete after 3 hours. After removal of the catalyst by filtration and evaporation of the solvent, 0.33 g (95%) of trans-2-(4-methylaminomethyl-cyclohexyl)-ethanol were obtained as a colorless oil, MS: 172 (MH+).

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-88df80d51213460c965ce9f4bfd786ce
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

Loading…