Acetic Acid → TERT-BUTYL 4-(1-CYANO-2-ETHOXY-2-OXOETHYLIDENE)PIPERIDINE-1-CARBOXYLATE

HRID 2054455노트

반응식

HRID 2054455 반응식
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].C([O-])(=O)C.[NH4+].C(O)(=O)C.O=[C:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1>C1C=CC=CC=1.C(OCC)(=O)C.O>[C:1]([C:3](=[C:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 517165Ammonium AcetateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

생성물 1

HCID 11551073TERT-BUTYL 4-(1-CYANO-2-ETHOXY-2-OXOETHYLIDENE)PIPERIDINE-1-CARBOXYLATE

시약·촉매·용매 3

HCID 241Benzene용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

Ethyl cyanoacetate (11.0 mL, 126 mmol), ammonium acetate (0.976 g, 12.6 mmol) and acetic acid (0.715 mL, 12.6 mmol) were added to a solution of tert-butyl 4-oxopiperidine-1-carboxylate 8-1 (25.0 g, 126 mmol) in 200 mL of benzene at ambient temperature. After stirring at reflux with azeotropic removal of water (Dean-Stark apparatus), the reaction mixture was cooled to ambient temperature and diluted with ethyl acetate (500 mL). The organics were washed with saturated aqueous sodium bicarbonate, brine, dried (magnesium sulfate), and concentrated in vacuo to give a crude residue. Purification of the crude residue by recrystallization from 10% ethyl acetate/hexanes afforded 8-2 as a white crystalline solid.

후처리

  1. washThe organics were washed with saturated aqueous sodium bicarbonate, brine
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated in vacuo
  4. customto give a crude residue
  5. customPurification of the crude residue
  6. customby recrystallization from 10% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-8c41c1eaa8ec485a91e8bd312e56cf16
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07329673B2

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