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

HRID 538918ノート

反応式

HRID 538918 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-316e1074022f443ab28467a8b23420f5
出典データセット
uspto-grants-2014_10
特許番号
US08865894B2

反応ノート

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