N-[1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-[(phenylmethyl)amino]propyl]Heptanamide → HCID 53653931, compound

HRID 2258053Notes

Reaction equation

HRID 2258053 reaction equation
[CH3:1][C:2]([Si:5]([CH3:29])([CH3:28])[O:6][CH2:7][CH:8]([NH:19][C:20](=[O:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:9]([NH:11]CC1C=CC=CC=1)[CH3:10])([CH3:4])[CH3:3]>CO.[OH-].[OH-].[Pd+2]>[NH2:11][CH:9]([CH3:10])[CH:8]([NH:19][C:20](=[O:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:7][O:6][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:28])[CH3:29]

Participants

4

Reactant 1

HCID 54006528N-[1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-[(phenylmethyl)amino]propyl]Heptanamide

Product 1

HCID 53653931HCID 53653931, compoundYield 102.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 28c (208.6 g, 0.50 mmol) and 104 mg of Pd(OH)2 in 15 mL of methyl alcohol is shaken in a Parr apparatus under hydrogen pressure for 18 h. The reaction mixture is filtered through diatomaceous earth and the filtrate concentrated to give 169 mg of the desired product 25c as an oil. NMR δ 0.84 (s, 9H), 1.05 (d, 3H), 1.60 (m, 2H), 2.10 (t, 2H), 3.31 (m, 1H), 6.47 (br d, 1H).

Workup

  1. filtrationThe reaction mixture is filtered through diatomaceous earth
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-cfb91f4e4699437c8f9a3f56311fec48
Source dataset
uspto-grants-1997_08
Patent number
US05658945

Reaction notes

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