HCID 9924295, 화합물 → HCID 69969745, 화합물

HRID 1280725노트

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HRID 1280725 반응식
[F:1][CH:2]([CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:3][N:4]1[CH2:8][CH2:7][C@@H:6]([S:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH2:5]1.[OH:25]OS([O-])=O.[K+]>CO>[F:1][CH:2]([CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:3][N:4]1[CH2:8][CH2:7][CH:6]([S:9]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[O:25])[CH2:5]1

참가 물질

4

반응물 2

HCID 9924295HCID 9924295, 화합물HCID 23707502Potassium hydroxy sulfite

생성물 1

HCID 69969745HCID 69969745, 화합물수율 10.2%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

(2RS,3R)-4-[1-(2-Fluoro-4-phenyl-butyl)-pyrrolidin-3-ylsulfanyl]-phenol (0.56 g, 1.62 mmol) was dissolved in MeOH (50 ml), cooled to 0° C. and treated with oxone (0.5 g, 0.81 mmol). After 4 hours stirring at 0° C., reaction mixture was quenched with saturated NaHCO3 (65 ml). Aqueous phase was extracted with CH2Cl2 (6 times). Combined organic phases were dried over Na2SO4 and the solvent was evaporated. The residue was chromatographed by MPLC over silica gel (CH2Cl2—MeOH, 99:1 then 98:2) then by preparative HPLC (EtOH-heptane, 08:92, detection at 254 nm) to provide (2R,3R, S-oxide R)-4-[1-(2-fluoro-4-phenyl-butyl)-pyrrolidine-3-sulfinyl]-phenol (30 mg, first fraction, 5%), MS: m/e=362.2 (M+H+).

후처리

  1. customreaction mixture
  2. customwas quenched with saturated NaHCO3 (65 ml)
  3. extractionAqueous phase was extracted with CH2Cl2 (6 times)
  4. dry with materialCombined organic phases were dried over Na2SO4
  5. customthe solvent was evaporated
  6. customThe residue was chromatographed by MPLC over silica gel (CH2Cl2—MeOH, 99:1

출처 및 근거

ORD 기록
ord-b95285b7f9f449efb71a3b5ce80a85ac
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06451819B2

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