Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | 3-(4-Methylbenzene-1-sulfonyl)-3-azabicyclo[3.2.0]heptan-6-one | HCID 21892510 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 59295122 | HCID 59295122 | 90.6% |
Reaction Steps
To a solution of 3-[(4-methylphenyl)sulfonyl]-3-azabicyclo[3.2.0]heptan-6-one (120 mg, 0.45 mmol) in EtOH:DCM (6 mL, 5:1) at 0° C. was added NaBH4 (21 mg, 0.54 mmol) portion-wise. After stirring at 25° C. for 0.5 hr, the solution was concentrated and then partitioned between DCM and water. The aqueous layer was extracted several times with DCM. The organic fractions were combined, concentrated and purified by column chromatography (silica, 0-0.5% MeOH in DCM (0.5% NH4OH)) affording the title compound as a white solid (109 mg, 90%): LC/MS (ES) m/e 268 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07709472B2 |
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| Source dataset | uspto-grants-2010_05 |
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| ORD ID | ord-687a730327a34036b8cf50adc73351bf |
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| Source note | uspto-grants-2010_05 |
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