Water → HCID 66797877、化合物

HRID 1677935ノート

反応式

HRID 1677935 の反応式
[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]

参加物

7

反応物 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

生成物 1

HCID 66797877HCID 66797877、化合物収率 72%

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 180Acetone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-394c26534c54441b8c57a4f461fcf25a
出典データセット
uspto-grants-2011_08
特許番号
US08008307B2

反応ノート

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