Potassium hydroxy sulfite → 3-[4-(2-Cyano-benzenesulfinyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 503935ノート

反応式

HRID 503935 の反応式
[OH:1]OS([O-])=O.[K+].[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]#[N:33])=[CH:21][C:20]=2[O:34][CH3:35])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>O.CO.C(#N)C>[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]#[N:33])=[O:1])=[CH:21][C:20]=2[O:34][CH3:35])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

参加物

6

反応物 2

HCID 23707502Potassium hydroxy sulfiteHCID 594284293-[4-(2-Cyano-phenylsulfanyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 668771343-[4-(2-Cyano-benzenesulfinyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒

実験手順

A solution of OXONE™ (0.470 g, 0.7636 mmol) in water (5 mL) was added to a solution of 3-[4-(2-cyano-phenylsulfanyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.209 g, 0.5091 mmol) in a mixture of MeOH (5 mL) and acetonitrile (5 mL). The reaction mixture was stirred at room temperature for 3 hours, then water was added and the mixture was extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over Na2SO4, filtered, and evaporated under reduced pressure. The resulting crude material was purified via flash chromatography (hexane/EtOAc, 7/3) to give 0.215 g of 3-[4-(2-cyano-benzenesulfinyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (not shown in Scheme O) as a clear oil.

後処理

  1. extractionthe mixture was extracted with EtOAc
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe resulting crude material was purified via flash chromatography (hexane/EtOAc, 7/3)

出典と根拠

ORDレコード
ord-d3097b7aa9a34fc6928048ea4c2cf557
出典データセット
uspto-grants-2010_08
特許番号
US07776910B2

反応ノート

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