Ethyl Acrylate → 1-tert-Butyl 3-ethyl 4-oxopyrrolidine-1,3-dicarboxylate

HRID 456342

反応式

HRID 456342 の反応式
CO[C:3](=[O:13])[CH2:4][NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[C:14]([O:18][CH2:19][CH3:20])(=[O:17])[CH:15]=[CH2:16].CC([O-])(C)C.[K+]>C1COCC1>[CH2:19]([O:18][C:14]([CH:15]1[C:3](=[O:13])[CH2:4][N:5]([C:6]([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7])[CH2:16]1)=[O:17])[CH3:20]

参加物

5

反応物 3

HCID 8821Ethyl AcrylateHCID 637609N-Boc-glycine methyl esterHCID 23665647Potassium tert-butoxide

生成物 1

HCID 108689421-tert-Butyl 3-ethyl 4-oxopyrrolidine-1,3-dicarboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

To a solution of BOC glycine methyl ester (J. Med. Chem. 2001, 44, 8, 1192-1201) (19.2 g, 101.5 mmol) in THF at 0° C. was added dropwise ethyl acrylate (11 mL, 101.5 mmol) over 10 minutes. The solution was stirred for 20 minutes, then KOtBu (111.65 mL, 111.65 mmol) was added over 45 minutes. The solution was allowed to warm to 25° C. overnight. The resulting solution concentrated in vacuo and portioned between ethyl acetate and water containing 5 mL of acetic acid. The ethyl acetate layer was removed and aqueous layer extracted with 2×200 mL of ethyl acetate. The combined ethyl acetate layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford an oil. MS (DCI/NH4) m/z=258 (M+H)+, 275 (M+NH4)+.

後処理

  1. concentrationThe resulting solution concentrated in vacuo
  2. customThe ethyl acetate layer was removed
  3. extractionaqueous layer extracted with 2×200 mL of ethyl acetate
  4. washThe combined ethyl acetate layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford an oil

出典と根拠

ORDレコード
ord-4b15624d75e04b23acafc39493a16c7c
出典データセット
uspto-grants-2013_07
特許番号
US08497275B2

関連ノート

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