Sodium hydride → (3aS,7aR)-hexahydrobenzo[d]oxazol-2(3H)-one

HRID 539080ノート

反応式

HRID 539080 の反応式
O[C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:8][C:9](=[O:15])[O:10]C(C)(C)C.[H-].[Na+].[NH4+].[Cl-]>C1COCC1>[O:15]1[C@@H:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]2[NH:8][C:9]1=[O:10]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11333385tert-butyl ((1S,2R)-2-hydroxycyclohexyl)carbaMate

生成物 1

HCID 10877202(3aS,7aR)-hexahydrobenzo[d]oxazol-2(3H)-one収率 66.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of tert-butyl (1S,2R)-2-hydroxycyclohexylcarbamate (1.15 g, 5.34 mmol) in THF (40 mL) was added NaH (60%, 0.32 g, 8.0 mmol) at 0° C. The reaction mixture was stirred at ambient temperature overnight. Saturated aqueous NH4Cl solution was added to quench the reaction. The mixture was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by column chromatography (EtOAc/hexanes, 2:1) to give (3aS,7aR)-hexahydrobenzo[d]oxazol-2(3H)-one (0.50 g, 66%) as a white solid.

後処理

  1. customto quench
  2. customthe reaction
  3. customThe mixture was partitioned between EtOAc and water
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (EtOAc/hexanes, 2:1)

出典と根拠

ORDレコード
ord-73db86f2acf345ecbad25538a8909e25
出典データセット
uspto-grants-2014_10
特許番号
US08865726B2

反応ノート

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