Ethyl Acetate → (3aS,7aS)-octahydro-1,3-benzoxazol-2-one

HRID 538918노트

반응식

HRID 538918 반응식
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-])=O)=[O:3].CCN(C(C)C)C(C)C.CCOC(C)=O.C([O-])(O)=O.[Na+]>ClCCCl>[O:4]1[C@H:5]2[CH2:10][CH2:9][CH2:8][CH2:7][C@@H:6]2[NH:11][C:2]1=[O:3]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 34143642-Nitrophenyl chloroformate

생성물 1

HCID 11768667(3aS,7aS)-octahydro-1,3-benzoxazol-2-one수율 75%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

The (1S,2S)-2-Aminocyclohexanole (750 mg, 6.51 mmol) and the 2-Nitrophenyl chloroformate (1378 mg, 6.84 mmol) were stirred in DCE (15 mL) with DIEA (2.39 mL, 13.68 mmol) in a sealed vial at 90° C. for 1 h. The reaction mixture was given into a separating funnel with 50 mL EtOAc and 50 mL saturated NaHCO3 solution. The aqueous layer was washed with 50 mL EtOAc. The organic layers were combined and washed with 50 mL H2O, 50 mL brine, dried with Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (hexane/EtOAc: 7:3→3:7) to give the title compound (770 mg, 5.13 mmol). tR: 0.69 min (LC-MS 1); 1H NMR (400 MHz, <dmso>) δ ppm 1.19-1.44 (m, 3H) 1.45-1.61 (m, 1H) 1.65 (d, J=9.77 Hz, 1H) 1.76 (d, J=11.34 Hz, 1H) 1.82-1.93 (m, 1H) 1.93-2.10 (m, 1H) 3.03-3.23 (m, 1H) 3.74 (td, J=11.34, 3.52 Hz, 1H) 7.53 (br. s., 1H)

후처리

  1. washThe aqueous layer was washed with 50 mL EtOAc
  2. washwashed with 50 mL H2O, 50 mL brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (hexane/EtOAc: 7:3→3:7)

출처 및 근거

ORD 기록
ord-316e1074022f443ab28467a8b23420f5
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865894B2

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