Sodium borohydride → 2-Hydroxybicyclo[3.2.0]heptan-6-one
Reaction equation
C([O:3][C:4]1(OCC)[CH2:10][CH:9]2[CH:5]1[CH2:6][CH2:7][C:8]2=[O:11])C.[BH4-].[Na+]>O1CCOCC1.OP([O-])(O)=O.[K+].Cl>[OH:11][CH:8]1[CH2:7][CH2:6][CH:5]2[CH:9]1[CH2:10][C:4]2=[O:3]Participants
6
Procedure
To a stirred solution of compound 1F in dioxane (50 mL) and 2M KH2PO4 (50 mL) was added NaBH4 (1.0 g, 26.4 mmol) over a 10 min-period, and the stirring was continued at RT for 1 hr. The reaction mixture was diluted with 2M HCl to adjust pH to 1, and stirred at RT for another 1 hr. The reaction was concentrated, dissolved in EtOAc, washed with water, dried over Na2SO4, and concentrated. Purification by silica gel chromatography (50% EtOAc in hexanes) provided the title compound (1.9 g) as a pale yellow oil.
Workup
- concentrationThe reaction was concentrated
- dissolutiondissolved in EtOAc
- washwashed with water
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customPurification by silica gel chromatography (50% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-479eea0990784411930dc1e50887c603
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07732480B2
Reaction notes
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