HCID 9924295、化合物 → HCID 69969745、化合物

HRID 1280725ノート

反応式

HRID 1280725 の反応式
[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

参加物

4

反応物 2

HCID 9924295HCID 9924295、化合物HCID 23707502Potassium hydroxy sulfite

生成物 1

HCID 69969745HCID 69969745、化合物収率 10.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

(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+).

後処理

  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

出典と根拠

ORDレコード
ord-b95285b7f9f449efb71a3b5ce80a85ac
出典データセット
uspto-grants-2002_09
特許番号
US06451819B2

反応ノート

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