Ethyl Acetate → ethyl (2S)-1-(1,3-benzothiazol-2-yl)-2-piperidinecarboxylate

HRID 412664노트

반응식

HRID 412664 반응식
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[C:17]([O:19][CH2:20][CH3:21])=[O:18].Cl.C(N(CC)CC)C.C(OCC)(=O)C>C1(C)C(C)=CC=CC=1.[Cu]>[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 11130Triethylamine hydrochlorideHCID 119872-ChlorobenzothiazoleHCID 736055Ethyl (2S)-2-piperidinecarboxylate

생성물 1

HCID 57016205ethyl (2S)-1-(1,3-benzothiazol-2-yl)-2-piperidinecarboxylate수율 81.9%

시약·촉매·용매 2

HCID 23978Copper촉매HCID 7237O-Xylene용매

실험 절차

2-Chloro-1,3-benzothiazole (503 mg) was added to a suspension of ethyl (2S)-2-piperidinecarboxylate (471 mg) [J.A.C.S. (1993), 115(22), 9925-9938], triethylamine hydrochloride (414 mg) and copper powder (38 mg) in xylene (5 ml). The reaction mixture was refluxed for 28 hours, after which time ethyl acetate (20 ml) was added to the cooled mixture and the solids filtered off. The organic layer was washed with water, dried over magnesium sulphate and the solvent removed under reduced pressure to afford ethyl (2S)-1-(1,3-benzothiazol-2-yl)-2-piperidinecarboxylate (705 mg) as a brown solid.

후처리

  1. temperatureThe reaction mixture was refluxed for 28 hours
  2. filtrationthe solids filtered off
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent removed under reduced pressure

출처 및 근거

ORD 기록
ord-dc04ecab06f84771aa20652422f9cdc2
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562964B1

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