Boron → (3S)-4,4-Dimethoxytetrahydro-2H-pyran-3-ol

HRID 1747104Notes

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]>>[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

Reactant 2

HCID 5462311Boron

HCID 118486434,4-Dimethoxyoxan-3-one

Product 1

HCID 66979040(3S)-4,4-Dimethoxytetrahydro-2H-pyran-3-ol

Procedure

reacting 4,4-dimethoxydihydro-2H-pyran-3(4H)-one with a boron reducing agent and R-(+)-2-methyl-CBS-oxazaborolidine, over a period of at least six hours to provide the (S)-4,4-dimethoxytetrahydro-2H-pyran-3-ol in at least 60% enantiomeric excess.

Sources & evidence

ORD record: ord-911d0e93b86d4b6883e4bc78bb7636d5
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150532B2

Reaction notes

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