Potassium Hydroxide → Tert-butyl 4-[2-(1-benzothien-2-yl)-1-hydroxyethyl]piperazine-1-carboxylate

HRID 902270

反応式

HRID 902270 の反応式
Br[C:2](Br)=[CH:3][C:4]1[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[CH:5]=1.[N:14]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[OH-:27].[K+]>O1CCCC1.O>[S:8]1[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[CH:5]=[C:4]1[CH2:3][CH:2]([N:17]1[CH2:18][CH2:19][N:14]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15][CH2:16]1)[OH:27]

参加物

5

反応物 3

HCID 14797Potassium HydroxideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 865990472-(2,2-Dibromo-vinyl)benzo[b]thiophene

生成物 1

HCID 68851338Tert-butyl 4-[2-(1-benzothien-2-yl)-1-hydroxyethyl]piperazine-1-carboxylate収率 65.3%

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

反応条件

温度
70 °C

実験手順

A 50 mL round bottom flask was charged with 2-(2,2-dibromo-vinyl)-benzo[b]thiophene (1.0 g, 3.17 mmol), tert-butyl 1-piperazinecarboxylate (0.09 g, 4.76 mmol) and potassium hydroxide (0.71 g, 12.5 mmol). A solution of tetrahydrofuran:water (4:1) was added and the solution was heated to 70° C. for 18 hours. At the end of this time the solution was concentrated and the residue was diluted with a 2N aqueious solution of hydrochloric acid and extracted 3 times with ethyl acetate. The ethyl acetate was dried and concentrated and the residue subjected chromatography via Biotage (FLASH 40 M, silica, 60% ethyl acetate/hexane) to yield 0.75 g (65%) of tert-butyl 4-[2-(1-benzothien-2-yl)-1-hydroxyethyl]piperazine-1-carboxylate as an off white solid. MS (ES) m/z 305.1; HRMS: calcd for C19H26N2O3S, 362.1664; found (ESI, [M+H]+), 361.1569.

後処理

  1. concentrationAt the end of this time the solution was concentrated
  2. additionthe residue was diluted with a 2N aqueious solution of hydrochloric acid
  3. extractionextracted 3 times with ethyl acetate
  4. dry with materialThe ethyl acetate was dried
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-e2defb4bad244e568d4c54e8569a1400
出典データセット
uspto-grants-2008_04
特許番号
US07365076B2

関連ノート

読み込み中…