Sodium Hydroxide → 2-(Diphenylhydroxymethyl)-1-azabicyclo[2.2.1]heptan-3-ol

HRID 4977

Reaction equation

[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([OH:16])[CH:8]2[C:13](=[O:14])[CH:12]3[CH2:15][N:9]2[CH2:10][CH2:11]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[C:17]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([OH:16])[CH:8]2[CH:13]([OH:14])[CH:12]3[CH2:15][N:9]2[CH2:10][CH2:11]3)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: -78 °C

Procedure

2-(Diphenylhydroxymethyl)-1-azabicyclo[2.2.1]heptan-3-one (210 mg) was dissolved in THF (5 ml) at -78° C. under argon. Lithium aluminium hydride (3 ml, 1.0M in ether) was added and the mixture stirred at -78° C. for 30 min, and then warmed to room temperature whereupon the reaction mixture became homogeneous. Water (0.1 ml) was added followed by sodium hydroxide (0.35 ml, 3N) and water (0.35 ml) affording a granular precipitate. Solid sodium sulphate was added, the mixture was filtered and the filtrate evaporated. The resulting diol was used without further purification.

Workup

temperaturewarmed to room temperature whereupon the reaction mixture
customaffording a granular precipitate
filtrationthe mixture was filtered
customthe filtrate evaporated
customThe resulting diol was used without further purification

Sources & evidence

ORD record: ord-2296a711d5b9416e8708573c01ee1a3d
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05242930

Linked notes

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