Thiophene → (S)-3-Chloro-1-(thiophen-2-yl)propan-1-ol

HRID 217268ノート

反応式

HRID 217268 の反応式
S1C=CC=C1.ClCCC(Cl)=O.[Sn](Cl)(Cl)(Cl)Cl.[Cl:17][CH2:18][CH2:19][C:20]([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)=[O:21].[BH4-].[Na+].ClCCC(C1SC=CC=1)O.C(OC=C)(=O)CCC>C1C=CC=CC=1.C(O)C.CCCCCC>[Cl:17][CH2:18][CH2:19][C@@H:20]([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)[OH:21]

参加物

11

反応物 7

HCID 8030Thiophene2 回HCID 24287Tin tetrachlorideHCID 31247Vinyl butyrateHCID 693643-Chloropropionyl chlorideHCID 4311764Sodium borohydrideHCID 75678553-Chloro-1-(2-thienyl)-1-propanoneHCID 116583743-Chloro-1-(2-thienyl)-1-propanol

生成物 1

HCID 10236042(S)-3-Chloro-1-(thiophen-2-yl)propan-1-ol

試薬・触媒・溶媒 3

HCID 241Benzene溶媒HCID 702Ethanol溶媒HCID 8058Hexane溶媒

実験手順

Huiling et al. describe a preparation of (S)-(−)-3-N-methylamino-1-(2-thienyl)-1-propanol from thiophene. Thiophene is converted with 3-chloropropanoyl chloride in the presence of tin tetrachloride in benzene to 3-chloro-1-(2-thienyl)-1-propanone, which is reduced with sodium borohydride in ethanol to 3-chloro-1-(2-thienyl)-1-propanol. Kinetic resolution by transesterification using vinyl butanoate and lipase B from Candida antarctica as catalyst in hexane yielded (S)-3-chloro-1-(2-thienyl)-1-propanol, which is converted to (S)-3-iodo-1-(2-thienyl)-1-propanol using sodium iodide in acetone. Subsequent treatment with methylamine in tetrahydrofuran afforded (S)-(−)-3-N-methylamino-1-(2-thienyl)-1-propanol.

出典と根拠

ORDレコード
ord-f1269d96a897474d951894a3eb36b7d4
出典データセット
uspto-grants-2012_06
特許番号
US08193380B2

反応ノート

読み込み中…