HCID 57069727, compound → HCID 57034260, compound

HRID 2299617Notes

Reaction equation

HRID 2299617 reaction equation
C([N:8]([CH2:28][C@H:29]([O:38][Si:39]([CH2:44][CH3:45])([CH2:42][CH3:43])[CH2:40][CH3:41])[CH2:30][O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH:9]1[CH2:15][CH2:14][CH2:13][C:12]2[CH:16]=[CH:17][C:18]([O:20]CC3C=CC=CC=3)=[CH:19][C:11]=2[CH2:10]1)C1C=CC=CC=1.[H][H]>[Pd].CO>[O:31]([CH2:30][C@@H:29]([O:38][Si:39]([CH2:42][CH3:43])([CH2:44][CH3:45])[CH2:40][CH3:41])[CH2:28][NH:8][CH:9]1[CH2:10][C:11]2[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:12]=2[CH2:13][CH2:14][CH2:15]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 2

HCID 57069727HCID 57069727, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57034260HCID 57034260, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-benzyl-N-(3-benzyloxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-[(2S)-3-phenoxy-2-(triethylsilyloxy)propyl]amine (25 g) and 10% palladium on activated carbon (50% wet, 2.5 g) in methanol (250 ml) was stirred at room temperature in the presence of hydrogen at an atmospheric pressure for 5 hours. After filtration, the filtrate was evaporated in vacuo to give 8-[(2S)-3-phenoxy-2-(triethylsilyloxy)propylamino]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ol (17 g).

Workup

  1. filtrationAfter filtration
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-540cfdb9a4fc44779bb7677ea958f5a3
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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