Methyl morpholine oxide → 5-(2,3-Difluorophenyl)cycloheptane-1,2-diol

HRID 1666124ノート

反応式

HRID 1666124 の反応式
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:15][CH2:14]C=C[CH2:11][CH2:10]1.C[N+]1([O-])[CH2:22][CH2:21][O:20]CC1.S(=O)(O)[O-:25].[Na+]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:15][CH2:14][CH:22]([OH:25])[CH:21]([OH:20])[CH2:11][CH2:10]1

参加物

7

反応物 3

HCID 82029Methyl morpholine oxide2 回HCID 23665763Sodium BisulfiteHCID 579114735-(2,3-Difluorophenyl)cyclohept-1-ene

生成物 1

HCID 579114025-(2,3-Difluorophenyl)cycloheptane-1,2-diol

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 180Acetone溶媒2 回HCID 962Water溶媒

実験手順

See: D. A. Spiegel et al. Tetrahedron 2002, 58, 6545-6554. In a 250 mL round-bottomed flask (t=g) was added (Z)-5-(2,3-difluorophenyl)cyclohept-1-ene (1.249 g, 6.00 mmol) and NMO (1.546 g, 13.19 mmol) in Acetone (9 mL) and Water (0.18 mL) to give a white suspension. Osmium tetroxide (0.301 mL, 0.024 mmol) (2.5 wt % solution in 2-methyl-2-propanol) was added. The mixture was stirred at room temperature. NMO gradually dissolved within 30 minutes to become a yellow solution. 1 h: TLC showed complete conversion to a much polar spot. Sodium bisulfite (200 mg) was added and stirring continued for 30 minutes. Acetone was stripped off and the residue was extracted with EtOAc three times. The combined organic layers were washed with brine, dried and concentrated to a white solid (crude weight: 1.7 g). It was directly carried onto next reaction.

後処理

  1. customto give a white suspension
  2. custom1 h
  3. stirringstirring
  4. extractionthe residue was extracted with EtOAc three times
  5. washThe combined organic layers were washed with brine
  6. customdried
  7. concentrationconcentrated to a white solid (crude weight
  8. customIt was directly carried onto next reaction

出典と根拠

ORDレコード
ord-82f204d3c9864a6599c2776e56ce8538
出典データセット
uspto-grants-2011_10
特許番号
US08044043B2

反応ノート

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