Ammonia → (1S)-2-amino-1-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol

HRID 132802Notes

Reaction equation

HRID 132802 reaction equation
[CH2:1](O)[C@@H:2]([OH:11])[C@H:3]1[O:8][C:6](=O)[C:5](O)=[C:4]1[OH:10].[NH3:13].[CH3:14]O>>[NH2:13][CH2:1][C@@H:2]([C@H:3]1[CH2:4][O:10][C:6]([CH3:5])([CH3:14])[O:8]1)[OH:11]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887Methanol2×HCID 54675810Erythorbic Acid

Product 1

HCID 59734745(1S)-2-amino-1-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol

Procedure

Epoxide 22 was prepared (Y. L. Merrer et al., Tetrahed. Lett. 1988, 31, 1003; M. Pottie et al. 1991, 2, 329; A. H. Al-Hakim et al., Synthesis, 1985, 207) from inexpensive and enantiomerically pure D-isoascorbic acid. The epoxide was dissolved in a large excess of methanol and added to a large volume of a saturated solution of ammonia in methanol and allowed to stand for 24 hr. The solvent was evaporated to afford the aminoalcohol 23.

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b3b638a5e35343ec8a409e8a6450f4bd
Source dataset
uspto-grants-2008_06
Patent number
US07388118B2

Reaction notes

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