Dichloromethane → HCID 59295122、化合物

HRID 2233001ノート

反応式

HRID 2233001 の反応式
[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

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 218925103-Tosyl-3-azabicyclo[3.2.0]heptan-6-one

生成物 1

HCID 59295122HCID 59295122、化合物収率 90.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
25 °C

実験手順

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)+.

後処理

  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))

出典と根拠

ORDレコード
ord-687a730327a34036b8cf50adc73351bf
出典データセット
uspto-grants-2010_05
特許番号
US07709472B2

反応ノート

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