Water → HCID 66797877, 화합물

HRID 1747588노트

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HRID 1747588 반응식
[O:1]=[C:2]1[C@H:7]2[CH2:8][C@H:4]([CH:5]=[CH:6]2)[N:3]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[OH2:16].C[N+]1([O-])CC[O:21]CC1.S(=O)(O)[O-].[Na+]>CC(C)=O.[Os](=O)(=O)(=O)=O>[OH:16][C@H:6]1[C@@H:5]([OH:21])[C@H:4]2[CH2:8][C@@H:7]1[C:2](=[O:1])[N:3]2[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

참가 물질

7

반응물 4

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 11830665(1R,4S)-tert-Butyl 3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylateHCID 23665763Sodium Bisulfite

생성물 1

HCID 66797877HCID 66797877, 화합물수율 72%

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 180Acetone용매

실험 절차

To a solution of tert-butyl (1R,4S)-3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate (500. mg, 2.39 mmol) in acetone (20.0 mL) was added a 4% aqueous solution of osmium tetroxide in H2O (0.015 mL, 0.00239 mmol). To the resulting mixture was added a 10.2 M aqueous solution of N-methylmorpholine N-oxide (0.262 mL, 2.67 mmol) dropwise over 1 h. At this point, a 0.240 M solution of aqueous sodium bisulfite (1.00 mL, 0.240 mmol) was added, the mixture was filtered through celite and concentrated in vacuo. The residue was purified via silica gel chromatography eluting with a gradient of 20 to 70% EtOAc in DCM to afford the title compound (420. mg, 72%). LC/MS: Rt=0.94 min, ES+ 244 (FA standard).

후처리

  1. filtrationthe mixture was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified via silica gel chromatography
  4. washeluting with a gradient of 20 to 70% EtOAc in DCM

출처 및 근거

ORD 기록
ord-f52ae478111e431eb2d11f63c02c29bd
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150525B2

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