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

HRID 2054455ノート

反応式

HRID 2054455 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 241Benzene溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8c41c1eaa8ec485a91e8bd312e56cf16
出典データセット
uspto-grants-2008_02
特許番号
US07329673B2

反応ノート

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