(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 720863Notes

Reaction equation

HRID 720863 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-]>C(O)C.[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 ethanol (300 ml). The catalyst was collected by filtration, and washed with ethanol. The combined washings were evaporated under reduced pressure and the residue was triturated in diethyl ether to give the title compound (5.86 g). The mother liquors were chromatographed on a Biotage column eluting with toluene:ethanol: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 ethanol
  3. customThe combined washings were evaporated under reduced pressure
  4. customthe residue was triturated in diethyl ether

Sources & evidence

ORD record
ord-91531e0bb5c543209fe38cca58ef046e
Source dataset
uspto-grants-2006_11
Patent number
US07135600B2

Reaction notes

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