Dichloromethane → HCID 59295122, compound

HRID 2233001Notes

Reaction equation

HRID 2233001 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:17][CH:16]3[CH:13]([CH2:14][C:15]3=[O:18])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(Cl)Cl.[BH4-].[Na+]>CCO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH2:17][C@H:16]3[C@H:13]([CH2:14][C@H:15]3[OH:18])[CH2:12]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 218925103-(4-Methylbenzene-1-sulfonyl)-3-azabicyclo[3.2.0]heptan-6-one

Product 1

HCID 59295122HCID 59295122, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

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)+.

Workup

  1. concentrationthe solution was concentrated
  2. custompartitioned between DCM and water
  3. extractionThe aqueous layer was extracted several times with DCM
  4. concentrationconcentrated
  5. custompurified by column chromatography (silica, 0-0.5% MeOH in DCM (0.5% NH4OH))

Sources & evidence

ORD record
ord-687a730327a34036b8cf50adc73351bf
Source dataset
uspto-grants-2010_05
Patent number
US07709472B2

Reaction notes

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