(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 2118315Notes

Reaction equation

HRID 2118315 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-b7968b4102da469a83fb2c4434c4d573
Source dataset
uspto-grants-2008_10
Patent number
US07442837B2

Reaction notes

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