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

HRID 539080노트

반응식

HRID 539080 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-73db86f2acf345ecbad25538a8909e25
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865726B2

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