Methanol → Serinol

HRID 375909Notes

Reaction equation

HRID 375909 reaction equation
[O:1]1[O:3][CH2:2]1.[C:4]([N:12]=[C:13]=[O:14])(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C[OH:16]>>[NH2:12][CH:4]([CH2:2][OH:3])[CH2:5][OH:16].[C:4]([NH:12][C:13](=[O:1])[O-:14])(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 78210Benzoyl isocyanateHCID 449520Dioxirane

Product 2

HCID 68294SerinolHCID 18372916Benzoylcarbamate

Procedure

Alternatively, an enantiomeric 2-aminopropane-1,3-diol of the present invention is prepared by reducing a trans-propenoate 83, prepared from an appropriate aldehyde and a (carbalkoxymethylene)triphenylphosphorane in a conventional Wittig reaction, is reduced to a carbinol 84 and epoxidized under asymmetric conditions to an epoxycarbinol 85, which in turn, is condensed with a benzoylisocyanate to provide a benzoylcarbamate, 86 cyclized to an oxazolidinone 87, and cleaved to an aminopropanediol 88.

Sources & evidence

ORD record
ord-98c9b14e76d8402b8f4c87d047cb5dfe
Source dataset
uspto-grants-1996_01
Patent number
US05488061

Reaction notes

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