4-Allyl-4-amino-adamantan-1-ol → 4-Propyl-4-amino-adamantan-1-ol

HRID 38448Notes

Reaction equation

HRID 38448 reaction equation
[CH2:1]([C:4]1([NH2:15])[CH:11]2[CH2:12][C:7]3([OH:14])[CH2:8][CH:9]([CH2:13][CH:5]1[CH2:6]3)[CH2:10]2)[CH:2]=[CH2:3]>CO.[Pd]>[CH2:1]([C:4]1([NH2:15])[CH:5]2[CH2:6][C:7]3([OH:14])[CH2:8][CH:9]([CH2:10][CH:11]1[CH2:12]3)[CH2:13]2)[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 583808924-Allyl-4-amino-adamantan-1-ol

Product 1

HCID 583809144-Propyl-4-amino-adamantan-1-olYield 76.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-allyl-4-amino-adamantan-1-ol (3, 3.6 g, 17.4 mmol) in methanol (50 mL) was treated with 50 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 2.8 g of the title compound as diastereomeric mixture (4). Rt=0.21 min, 0.73 min (Method 3). Detected mass: 210.2 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-8020780015cb4042859ff91f19c9cd88
Source dataset
uspto-grants-2013_09
Patent number
US08524737B2

Reaction notes

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