HCID 14249478, compound → alpha-(Aminomethyl)-2,2-dimethyl-1,3-dioxolane-4-methanol

HRID 1589418Notes

Reaction equation

HRID 1589418 reaction equation
[N:1]([CH2:4][CH:5]([CH:7]1[CH2:11][O:10][C:9]([CH3:13])([CH3:12])[O:8]1)[OH:6])=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][CH:5]([CH:7]1[CH2:11][O:10][C:9]([CH3:13])([CH3:12])[O:8]1)[OH:6]

Participants

4

Reactant 1

HCID 14249478HCID 14249478, compound

Product 1

HCID 11971028alpha-(Aminomethyl)-2,2-dimethyl-1,3-dioxolane-4-methanolYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 9.36 g of 2-azido-1-(2,2,-dimethyl-1,3-dioxolan-4-yl)ethanol in 150 ml of methanol is combined with 900 mg of palladium/charcoal catalyst (10%). The hydrogenation is conducted for 1 hour under normal pressure. The mixture is then filtered off from the catalyst and washed with methanol. The combined solutions are concentrated to dryness under vacuum. The remaining oil is crystallized from ethanol/ether, thus obtaining 6.29 g (78% of theory) of 2-amino-1-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanol in white needles, mp 94°-96° C.

Workup

  1. filtrationThe mixture is then filtered off from the catalyst
  2. washwashed with methanol
  3. concentrationThe combined solutions are concentrated to dryness under vacuum
  4. customThe remaining oil is crystallized from ethanol/ether

Sources & evidence

ORD record
ord-0c3b4fdca9894b64bbf5b91d26572317
Source dataset
uspto-grants-1986_02
Patent number
US04570007

Reaction notes

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