2-Chloroethyl chloroformate → 6-chloro-3H-spiro[isobenzofuran-1,4'-piperidine]

HRID 270050ノート

反応式

HRID 270050 の反応式
C([N:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=3[CH2:15][O:14]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OCCCl)=O>ClCCl>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]2[CH2:15][O:14][C:11]3([CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[C:17]=2[CH:18]=1

参加物

4

反応物 2

HCID 123052-Chloroethyl chloroformateHCID 598336401'-Benzyl-6-chloro-3H-spiro[isobenzofuran-1,4'-piperidine]

生成物 1

HCID 468354386-chloro-3H-spiro[isobenzofuran-1,4'-piperidine]収率 28.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 1′-benzyl-6-chloro-3H-spiro[2-benzofuran-1,4′-piperidine] (850 mg, 2.7 mmol) in dichloromethane (CH2Cl2) (8 mL) was added chloroethyl chloroformate (Yang, B. V; o'Rourke, D; Li, J., Synlett, 1993, 195-196) (772 mg, 5.4 mmol) slowly at 0° C. After addition was complete the reaction mixture was stirred at 0° C. for 30 min. The volatiles were removed in vacuo, residue was dissolved in methanol (10 mL) and kept at reflux for 40 min. The volatiles were removed in vacuo and the residue was purified by silica gel flash chromatography (0-6% methanol in dichloromethane, 0.2% ammonium hydroxide (NH4OH)) to give the titled compound (170 mg) and 1′-benzyl-6-chloro-3H-spiro[2-benzofuran-1,4′-piperidine] was recovered (200 mg).

後処理

  1. additionAfter addition
  2. customThe volatiles were removed in vacuo, residue
  3. dissolutionwas dissolved in methanol (10 mL)
  4. temperatureat reflux for 40 min
  5. customThe volatiles were removed in vacuo
  6. customthe residue was purified by silica gel flash chromatography (0-6% methanol in dichloromethane, 0.2% ammonium hydroxide (NH4OH))

出典と根拠

ORDレコード
ord-51fb170678724e6b9680f23f8f15607d
出典データセット
uspto-grants-2008_11
特許番号
US07449475B2

反応ノート

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