1-Azido-4,4-dimethylhexan-2-ol → HCID 55289824, compound

HRID 1927648Notes

Reaction equation

HRID 1927648 reaction equation
[N:1]([CH2:4][CH:5]([OH:12])[CH2:6][C:7]([CH3:11])([CH3:10])[CH2:8][CH3:9])=[N+]=[N-]>[Pd].C(O)C>[NH2:1][CH2:4][CH:5]([OH:12])[CH2:6][C:7]([CH3:11])([CH3:10])[CH2:8][CH3:9]

Participants

4

Reactant 1

HCID 866441711-Azido-4,4-dimethylhexan-2-ol

Product 1

HCID 55289824HCID 55289824, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-azido-4,4-dimethylhexan-2-ol (54.8 g, 320 mmol), 5% Pd/C (4 g) and ethanol (500 mL) were stirred under hydrogen (40 psi) for 2 days. The reaction mixture was filtered through Celite and the filtrate was concentrated to provide the title compound. 1H NMR (500 MHz, CDCl3) δ 3.61 (m, 1H), 2.77 (dd, J=12.5 Hz, J=3.4 Hz, 1H), 2.49 (dd, J=12.5 Hz, J=8.9 Hz, 1H), 2.00 (brs, 2H), 1.30 (m, 3H), 1.24 (dd, J=14.5 Hz, J=2.6 Hz, 1H), 0.92 (s, 3H), 0.90 (s, 3H), 0.83 (t, J=7.5 Hz, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-20e6940a33bd4bf4a216729355fad696
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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