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

HRID 1666124노트

반응식

HRID 1666124 반응식
[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

참가 물질

7

반응물 3

HCID 82029Methyl morpholine oxide2회HCID 23665763Sodium BisulfiteHCID 579114735-(2,3-Difluorophenyl)cyclohept-1-ene

생성물 1

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

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 180Acetone용매2회HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-82f204d3c9864a6599c2776e56ce8538
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044043B2

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