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

HRID 270050노트

반응식

HRID 270050 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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).

후처리

  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))

출처 및 근거

ORD 기록
ord-51fb170678724e6b9680f23f8f15607d
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449475B2

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