(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaborole → 2H-PYRAN-3-OL, TETRAHYDRO-4,4-DIMETHOXY-, (3R)-

HRID 1747108Notes

Reaction equation

HRID 1747108 reaction equation
[CH3:1][O:2][C:3]1([O:10][CH3:11])[CH2:8][CH2:7][O:6][CH2:5][C:4]1=[O:9].[B].B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@H]2N1CCC2>>[CH3:1][O:2][C:3]1([O:10][CH3:11])[CH2:8][CH2:7][O:6][CH2:5][C@H:4]1[OH:9]

Participants

4

Reactant 3

HCID 2734713(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaboroleHCID 5462311BoronHCID 118486434,4-Dimethoxyoxan-3-one

Product 1

HCID 116654592H-PYRAN-3-OL, TETRAHYDRO-4,4-DIMETHOXY-, (3R)-

Procedure

reacting 4,4-dimethoxydihydro-2H-pyran-3(4H)-one with a boron reducing agent and S-(−)-2-methyl-CBS-oxazaborolidine, over a period of at least six hours to provide the (R)-4,4-dimethoxytetrahydro-2H-pyran-3-ol, wherein (R)-4,4-dimethoxytetrahydro-2H-pyran-3-ol is formed in at least 90% enantiomeric excess.

Sources & evidence

ORD record
ord-75ea4b947bde4a74b9b03d90869b0dea
Source dataset
uspto-grants-2015_10
Patent number
US09150532B2

Reaction notes

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