Sodium cyanoborohydride → trans N-{1-[2-(5-chloro-thiophen-2-yl)-cyclopropyl]-ethyl}-O-methyl-hydroxylamine

HRID 1807399ノート

反応式

HRID 1807399 の反応式
[CH3:1][O:2][N:3]=[C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[S:10][C:11]([Cl:14])=[CH:12][CH:13]=1)[CH3:5].C([BH3-])#N.[Na+]>C(O)(=O)C>[Cl:14][C:11]1[S:10][C:9]([C@@H:7]2[CH2:8][C@H:6]2[CH:4]([NH:3][O:2][CH3:1])[CH3:5])=[CH:13][CH:12]=1

参加物

4

反応物 2

HCID 5003444Sodium cyanoborohydrideHCID 86669077trans 1-[2-(5-Chloro-thiophen-2-yl)-cyclopropyl]-ethanone O-methyl-oxime

生成物 1

HCID 86669066trans N-{1-[2-(5-chloro-thiophen-2-yl)-cyclopropyl]-ethyl}-O-methyl-hydroxylamine収率 79%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a stirred solution of trans 1-[2-(5-Chloro-thiophen-2-yl)cyclopropyl]-ethanone O-methyl-oxime (1.2 g; 5.2 mmol) prepared as described in example P25, in acetic acid (15 ml) at ambient temperature was added portionwise sodium cyanoborohydride (1.0 g; 15.7 mmol). The reaction mixture was stirred for 16 hours at ambient temperature then poured on sodium hydroxide solution (0.5M; 150 ml) and extracted with dichloromethane (3×50 ml). Combined organic layers were dried over anhydrous sodium sulphate. The solvent was removed in vacuo and the residue was purified by flash chromatography over silica gel (elution gradient: cyclohexane/ethyl acetate 99:1 to 50:50) to afford 0.91 g (79% of theory) of trans N-{1-[2-(5-chloro-thiophen-2-yl)-cyclopropyl]-ethyl}-O-methyl-hydroxylamine as a mixture of diastereomeres in form of a clear viscous oil.

後処理

  1. additionthen poured on sodium hydroxide solution (0.5M; 150 ml)
  2. extractionextracted with dichloromethane (3×50 ml)
  3. dry with materialCombined organic layers were dried over anhydrous sodium sulphate
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by flash chromatography over silica gel (elution gradient: cyclohexane/ethyl acetate 99:1 to 50:50)

出典と根拠

ORDレコード
ord-b8f5968b79fc4d338df4cdcc91308f11
出典データセット
uspto-grants-2013_01
特許番号
US08357635B2

反応ノート

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