Nitrogen → 8-Methyl-3-azabicyclo[3.2.1]octan-8-ol

HRID 627335Notes

Reaction equation

HRID 627335 reaction equation
C([N:8]1[CH2:14][CH:13]2[C:15]([CH3:17])([OH:16])[CH:10]([CH2:11][CH2:12]2)[CH2:9]1)C1C=CC=CC=1.N#N>CO.[Pd]>[CH3:17][C:15]1([OH:16])[CH:13]2[CH2:12][CH2:11][CH:10]1[CH2:9][NH:8][CH2:14]2

Participants

5

Reactant 2

HCID 947NitrogenHCID 673558463-Benzyl-8-methyl-3-azabicyclo[3.2.1]octan-8-ol

Product 1

HCID 673554478-Methyl-3-azabicyclo[3.2.1]octan-8-olYield 103.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

A sample of 3-benzyl-8-methyl-3-azabicyclo[3.2.1]octan-8-ol (110 mg, 0.48 mmol) was dissolved in MeOH (20 ml) and the atmosphere was replaced with N2 (3×). 10% Pd/C (cat.) was added and the atmosphere was replaced with H2 (3×). The resulting reaction mixture was stirred at RT at balloon pressure overnight. When TLC showed no more UV active spot the Pd/C was filtered off (always keeping wet with MeOH) and the filtrate was concentrated which gave 8-methyl-3-azabicyclo[3.2.1]octan-8-ol (70 mg, 99% yield).

Workup

  1. customThe resulting reaction mixture
  2. filtrationwas filtered off (
  3. concentrationwas concentrated which

Sources & evidence

ORD record
ord-dfe025a085d44a7482726fbd4b931000
Source dataset
uspto-grants-2016_04
Patent number
US09309252B2

Reaction notes

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