1-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-cyclooctylamine → 5-Amino-5-propyl-cyclooctanol

HRID 402548Notes

Reaction equation

HRID 402548 reaction equation
[CH2:1]([C:4]1([NH2:20])[CH2:11][CH2:10][CH2:9][CH:8]([O:12][Si](C(C)(C)C)(C)C)[CH2:7][CH2:6][CH2:5]1)[CH:2]=[CH2:3]>CO.[Pd]>[NH2:20][C:4]1([CH2:1][CH2:2][CH3:3])[CH2:11][CH2:10][CH2:9][CH:8]([OH:12])[CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 1

HCID 685558261-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-cyclooctylamine

Product 1

HCID 685513705-Amino-5-propyl-cyclooctanolYield 87.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 895 mg (4.88 mmol) of 1-allyl-5-(tert-butyl-dimethyl-silanyloxy)-cyclooctylamine (63) in 15 mL of methanol was treated with 52 mg of 10% palladium on activated carbon and the mixture was stirred overnight under a hydrogen atmosphere (1 atm) at room temperature. The catalyst was removed by filtration, and the filtrate was evaporated in vacuo to give 0.794 g of the title compound (64). Rt=0.56 min, 0.62 min min (Method C). Detected mass: 186.3 (M+H+).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-592cb7ae22be4750bf42fa270a500f1b
Source dataset
uspto-grants-2014_06
Patent number
US08742116B2

Reaction notes

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