Cyclopentanone → 2-Cyclohexyl-3-oxo-3-(2-oxo-cyclopentyl)-propionic acid ethyl ester

HRID 889370ノート

反応式

HRID 889370 の反応式
[Li+].CC([N-]C(C)C)C.[C:9]1(=[O:14])[CH2:13][CH2:12][CH2:11][CH2:10]1.[CH2:15]([O:17][C:18](=[O:37])[CH:19]([CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[C:20](N1C2C=CC=CC=2N=N1)=[O:21])[CH3:16]>C1COCC1>[CH2:15]([O:17][C:18](=[O:37])[CH:19]([CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[C:20](=[O:21])[CH:10]1[CH2:11][CH2:12][CH2:13][C:9]1=[O:14])[CH3:16]

参加物

5

反応物 3

HCID 8452CyclopentanoneHCID 2724682Lithium diisopropylamideHCID 3722282ethyl 3-(1H-benzotriazol-1-yl)-2-cyclohexyl-3-oxopropanoate

生成物 1

HCID 673867762-Cyclohexyl-3-oxo-3-(2-oxo-cyclopentyl)-propionic acid ethyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

To a −78° C. cold solution of LDA (2 M solution in heptane/ethylbenzene/THF, 15.7 ml, 31 mmol) in THF (96 ml) under an argon atmosphere was added a solution of cyclopentanone (2.78 ml, 31 mmol; CAS Reg. No. 120-92-3) in THF (72 ml) within 25 min. The mixture was stirred for 2 h at −78° C. A solution of 3-benzotriazol-1-yl-2-cyclohexyl-3-oxo-propionic acid ethyl ester (9 g, 29 mmol) in THF (63 ml) was added and the solution was stirred at ambient temperature for 14 h. Ice water was added, the mixture was poured onto ice water/brine 1/1 and extracted two times with TBME. The combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. After filtration the solvent was removed under reduced pressure to give the title compound (8.8 g; quant.) which was used in the next step without further purification.

後処理

  1. stirringthe solution was stirred at ambient temperature for 14 h
  2. extractionextracted two times with TBME
  3. washThe combined extracts were washed with ice water/brine 1/1
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration the solvent
  6. customwas removed under reduced pressure

出典と根拠

ORDレコード
ord-473ae73027584a7cb4039ff0af716237
出典データセット
uspto-grants-2012_08
特許番号
US08252826B2

反応ノート

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