HCID 68947054, compound → HCID 67257610, compound

HRID 2190872Notes

Reaction equation

HRID 2190872 reaction equation
[ClH:1].[CH2:2]([O:4][C:5]1[CH:6]=[C:7]([C@@H:13]2[C@H:18]([NH:19][C@@H](C3C=CC=CC=3)C)[CH2:17][CH2:16][S:15][CH2:14]2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH3:3].[H][H]>[Pd].CO>[ClH:1].[CH2:2]([O:4][C:5]1[CH:6]=[C:7]([C@@H:13]2[C@H:18]([NH2:19])[CH2:17][CH2:16][S:15][CH2:14]2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH3:3]

Participants

5

Reactant 2

HCID 68947054HCID 68947054, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67257610HCID 67257610, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

A mixture of 3.6 g of 10% Pd catalyst on charcoal and 4 mmol of (3R,4R)-3-(3-ethoxy-4-methoxyphenyl)-N-[(1R)-1-phenylethyl]tetrahydro-2H-thiopyran-4-amine hydrochloride in 100 ml of methanol is hydrogenated with 110 mbar hydrogen pressure at reflux temperature for 5 h. Additional 3.6 g of the Pd catalyst are added and the hydrogenation is continued for further 5 h. The catalyst is filtered off and the filtrate concentrated yielding the title compound as a highly viscous resin which is used for the next reaction steps without further purification.

Workup

  1. temperatureat reflux temperature for 5 h
  2. filtrationThe catalyst is filtered off
  3. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-292a8f26c40e4f9aa6501f75fe0cee2a
Source dataset
uspto-grants-2012_12
Patent number
US08324404B2

Reaction notes

Loading…