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

HRID 1450745Notes

Reaction equation

HRID 1450745 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 δ0.84 (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-6355f0b8aafe4ff6be085930d3511c16
Source dataset
uspto-grants-1997_02
Patent number
US05602275

Reaction notes

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