Ethanol → HCID 66860142, compound

HRID 1696858Notes

Reaction equation

HRID 1696858 reaction equation
[OH:1][C@H:2]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[CH:32]=1)[CH2:3][NH:4][CH:5]([CH3:30])[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][NH:19]C(=O)OCC2C=CC=CC=2)=[CH:11][CH:10]=1.[CH2:38]([OH:40])C>[OH-].[OH-].[Pd+2].ClCCl>[OH-:1].[NH4+:4].[CH3:38][OH:40].[NH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][CH2:6][CH:5]([NH:4][CH2:3][C@@H:2]([C:31]2[CH:32]=[C:33]([OH:37])[CH:34]=[CH:35][CH:36]=2)[OH:1])[CH3:30])=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 702EthanolHCID 66861391HCID 66861391, compound

Product 2

HCID 21894508Ammonium hydroxide methanolYield 10%HCID 66860142HCID 66860142, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of butylcarbamate 141 (1.04 g, 2.06 mmol), palladium dihydroxide (0.20 g, 10% Pd(OH)2 on carbon, 50% wet) and ethanol (10 mL) was stirred at rt for 94 h under atmospheric hydrogen pressure. The catalyst was removed by filtration through diatomaceous earth and the filtrate was concentrated by rotary evaporation. Purification by column chromatography (silica, a gradient of 0:100 to 10:90 (10% concentrated ammonium hydroxide/methanol)/dichloromethane) gave desired amine 142 (0.63 g, 83% yield) as a tan solid: 1H NMR (500 MHz, CDCl3) δ 1.16-1.29 (m, 3H), 1.48-1.74 (m, 8H), 2.50-2.60 (m, 4H), 2.92-3.30 (m, 5H), 4.83 (br s, 1H), 6.71-6.72 (m, 1H), 6.83-6.85 (m, 2H), 7.00-7.15 (m, 5H); m/z (ESI) 371 [C23H34N2O2+H]+.

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. concentrationthe filtrate was concentrated by rotary evaporation
  3. customPurification by column chromatography (silica

Sources & evidence

ORD record
ord-1463d69eb2de462e8d7d9302134a2e13
Source dataset
uspto-grants-2012_04
Patent number
US08163758B2

Reaction notes

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