Triethylamine → HCID 21833725, 화합물

HRID 617734노트

반응식

HRID 617734 반응식
C[N:2]1[CH2:7][CH2:6][C:5]2([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[O:10][CH2:9][CH2:8]2)[CH2:4][CH2:3]1.C(N(C(C)C)CC)(C)C.Cl[C:27]([O:29][CH:30](Cl)[CH3:31])=[O:28].C(N(CC)CC)C.ClC(OCC)=O.C([O-])([O-])=O.[Na+].[Na+]>ClC(Cl)C.ClCCl.C1COCC1>[CH2:30]([O:29][C:27]([N:2]1[CH2:7][CH2:6][C:5]2([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[O:10][CH2:9][CH2:8]2)[CH2:4][CH2:3]1)=[O:28])[CH3:31]

참가 물질

10

반응물 6

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformateHCID 21833714HCID 21833714, 화합물

생성물 1

HCID 21833725HCID 21833725, 화합물수율 102.6%

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 63651,1-Dichloroethane용매HCID 8028Tetrahydrofuran용매

실험 절차

A stirred solution of 2,3-dihydro-1'-methylspiro[4H-benzopyran-4,4'-piperidine] (D3, 1.0 g, 0.0046 mole) and diisopropylethylamine (1.2 ml, 0.0070 mole) in dichloroethane (20 ml) was treated with 1-chloroethyl chloroformate (0.64 ml, 0.0060 mole) and kept at room temp. for 1 h followed by 20 mins at reflux. The solution was then concentrated in vacuo and the residue treated with methanol (20 ml) and heated under reflux for 2 h. The reaction mixture was concentrated in vacuo to leave a beige solid, which was dissolved in dichloromethane (50 ml) and THF (10 ml) and treated with triethylamine (0.84 ml, 0.0060 mole) followed by ethyl chloroformate (0.44 ml, 0.0046 mole). The solution was stirred at room temperature for 2 h, then treated with 10% Na2CO3 solution (20 ml) and extracted with dichloromethane (2×40 ml). The combined extract was dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 1:1 ether/60-80 petrol to afford the title compound as a yellow oil (1.3 g, 100%).

후처리

  1. waitfollowed by 20 mins
  2. temperatureat reflux
  3. concentrationThe solution was then concentrated in vacuo
  4. additionthe residue treated with methanol (20 ml)
  5. temperatureheated
  6. temperatureunder reflux for 2 h
  7. concentrationThe reaction mixture was concentrated in vacuo
  8. customto leave a beige solid, which
  9. extractionextracted with dichloromethane (2×40 ml)
  10. extractionThe combined extract
  11. dry with materialwas dried (Na2SO4)
  12. concentrationconcentrated in vacuo
  13. customThe residue was chromatographed on silica gel eluting with 1:1 ether/60-80 petrol

출처 및 근거

ORD 기록
ord-3ac770cd2ac64bed863a176117bf1da5
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05952325

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