HCID 86585785, compound → HCID 86585783, compound

HRID 1351893Notes

Reaction equation

HRID 1351893 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].C([N:13]([CH:25]1[CH2:31][C:30]2[CH:32]=[C:33]([O:36][CH2:37][C:38]([NH2:40])=[O:39])[CH:34]=[CH:35][C:29]=2[CH2:28][CH2:27][CH2:26]1)[CH2:14][C@H:15]([OH:24])[CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[OH:24][C@H:15]([CH2:16][O:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:14][NH:13][CH:25]1[CH2:31][C:30]2[CH:32]=[C:33]([O:36][CH2:37][C:38]([NH2:40])=[O:39])[CH:34]=[CH:35][C:29]=2[CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 2

HCID 86585785HCID 86585785, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86585783HCID 86585783, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-[8-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]acetamide methanesulfonate (240 mg) and 10% palladium on activated carbon (50% wet, 50 mg) in ethanol (5 ml) was stirred at room temperature in the presence of hydrogen at an atmospheric pressure for 2 hours. After filtration, the filtrate was evaporated in vacuo and followed by trituration with diisopropyl ether to give 2-[8-[(2S)-2-hydroxy-3-phenoxypropyl]amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]acetamide methanesulfonate (187 mg).

Workup

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

Sources & evidence

ORD record
ord-870c5b56d1694408a0350ccf306e8b6b
Source dataset
uspto-grants-2007_05
Patent number
US07217706B2

Reaction notes

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