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

HRID 412664ノート

反応式

HRID 412664 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 7237O-Xylene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-dc04ecab06f84771aa20652422f9cdc2
出典データセット
uspto-grants-2003_05
特許番号
US06562964B1

反応ノート

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