Water → HCID 67270991, 화합물

HRID 1039702

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HRID 1039702 반응식
[F:1][C@@H:2]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH:4]=[CH2:5].C([OH:24])(C)(C)C.C[N+]1([O-])CCOCC1.S([O-])([O-])=O.[Na+].[Na+].[OH2:39]>[Os]>[F:1][C@H:2]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH:4]([OH:24])[CH2:5][OH:39]

참가 물질

7

반응물 5

HCID 962Water2회HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 86635707HCID 86635707, 화합물

생성물 1

HCID 67270991HCID 67270991, 화합물

시약·촉매·용매 1

HCID 23937Osmium촉매

반응 조건

온도
23 °C

실험 절차

To a 250 mL RBF containing tert-butyl (1S,2R)-1-fluoro-1-phenylbut-3-en-2-ylcarbamate (105.00 mg, 396 mmol)(mixture of diasteromers at benzylic fluoride stereocenter) was added tert-butanol (3 mL) and water (1 ml). The mixture was allowed to stir at 23° C. for 2 min, then NMO (139 mg, 1187 mmol) and osmium tetraxide (124 μA, 396 mmol) were added and the reaction was allowed to stir for another 48 h. before the reaction was quenched with water and sodium sulfite (1496 mg, 11872 mmol). The reaction was allowed to stir for 15 min and then extracted with EtOAc (3×). The combined organics were washed with HCl (1 N), sodium bicarbonate, brine and dried over sodium sulfate. The dried solution was passed through a plug of silica gel and concentrated to give 102 mg of a colorless oil

후처리

  1. stirringto stir for another 48 h. before the reaction
  2. stirringto stir for 15 min
  3. extractionextracted with EtOAc (3×)
  4. washThe combined organics were washed with HCl (1 N), sodium bicarbonate, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-fc1aa90153f141789ea0a6c8dcf5e13c
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552181B2

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