(1R)-2-Azido-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol → (1R)-2-Amino-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-YL)ethanol

HRID 857095Notes

Reaction equation

HRID 857095 reaction equation
[N:1]([CH2:4][C@@H:5]([C:7]1[CH:18]=[CH:17][C:10]2[O:11][C:12]([CH3:16])([CH3:15])[O:13][CH2:14][C:9]=2[CH:8]=1)[OH:6])=[N+]=[N-]>CCO.[Pd]>[NH2:1][CH2:4][C@@H:5]([C:7]1[CH:18]=[CH:17][C:10]2[O:11][C:12]([CH3:15])([CH3:16])[O:13][CH2:14][C:9]=2[CH:8]=1)[OH:6]

Participants

4

Reactant 1

HCID 86595260(1R)-2-Azido-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

Product 1

HCID 56600231(1R)-2-Amino-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-YL)ethanolYield 38.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(1R)-2-Azido-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol (16.99 g) was hydrogenated over 10% Pd—C (1 g) in EtOH (300 ml). The catalyst was collected by filtration, and washed with EtOH. The combined washings were evaporated under reduced pressure and the residue was triturated in ether to give the title compound (5.86 g). The mother liquors were chromatographed on a Biotage column eluting with toluene:EtOH:aqueous ammonia (85:14:1) to give a further batch of the title compound (5.99 g). LCMS RT=1.68 min, ES+ve 206 (MH—H2O)+.

Workup

  1. filtrationThe catalyst was collected by filtration
  2. washwashed with EtOH
  3. customThe combined washings were evaporated under reduced pressure
  4. customthe residue was triturated in ether

Sources & evidence

ORD record
ord-d8335fec501547babc0dda5efd845114
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

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