7-Benzyloxy-2-phenyl-4-piperidin-1-yl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester → 7-Hydroxy-2-phenyl-4-piperidin-1-yl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

HRID 642381Notes

Reaction equation

HRID 642381 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:9]2[N:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[S:20][C:8]=2[C:7]=1[O:27]CC1C=CC=CC=1)=[O:5])[CH3:2]>C(O)C.C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[C:9]2[N:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[S:20][C:8]=2[C:7]=1[OH:27])=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 684281247-Benzyloxy-2-phenyl-4-piperidin-1-yl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

Product 1

HCID 684277447-Hydroxy-2-phenyl-4-piperidin-1-yl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl esterYield 101.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7-benzyloxy-2-phenyl-4-piperidin-1-yl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (47 mg, 0.10 mmole) and 10% Pd/C (20 mg) in a mixture of ethanol and ethyl acetate (3 ml, 1:5) was hydrogenated at room temperature for 7 h before it was filtered, washed with ethyl acetate and concentrated in vacuo to give the title compound as a yellow oil (39 mg). MS: (+) m/z 384.34 (M+1), MS: (−) m/z 382.37 (M−1).

Workup

  1. filtrationwas filtered
  2. washwashed with ethyl acetate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-67bc49fd98e84b718080ce16089dd985
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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