Hydrochloric Acid → 1H-Cyclopropa[4,5]cyclopenta[1,2]pyrazole-3-carboxylic acid, 4,4a,5,5a-tetrahydro-, ethyl ester, (4aR,5aR)-

HRID 1623937ノート

反応式

HRID 1623937 の反応式
[C@@H:1]12[CH2:6][C@@H:5]1[CH2:4][CH2:3][C:2]2=O.CC(C)([O-])C.[K+].[C:14](OCC)(=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16].[NH2:24][NH2:25].Cl>C(O)C>[CH2:6]1[C@@H:5]2[CH2:4][C:3]3[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:24][NH:25][C:2]=3[C@H:1]12

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 9321HydrazineHCID 11615157(1R,5S)-bicyclo[3.1.0]hexan-2-oneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 589068031H-Cyclopropa[4,5]cyclopenta[1,2]pyrazole-3-carboxylic acid, 4,4a,5,5a-tetrahydro-, ethyl ester, (4aR,5aR)-収率 17.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

(1R,5S)-Bicyclo[3.1.0]hexan-2-one (1.000 g, 10.40 mmol) was taken up in ethanol (40 mL) and potassium tert-butoxide (1.0 M in THF) (13.00 mL, 13.00 mmol) was added, followed by diethyl oxalate (1.413 mL, 10.40 mmol). The resulting solution was heated and stirred for 1 h at 70° C. Hydrazine (10.40 mL, 10.40 mmol) was then added, followed by hydrochloric acid (ca 3 M aqueous) (10.40 mL, 31.2 mmol). The solution was stirred at 70° C. for 1 h and purified by HPLC to give the title compound (356 mg, 1.852 mmol, 17.80% yield) as a solid. LCMS m/z=193.3 [M+H]+.

後処理

  1. temperatureThe resulting solution was heated
  2. stirringThe solution was stirred at 70° C. for 1 h
  3. custompurified by HPLC

出典と根拠

ORDレコード
ord-b0669d0a1ba94091b5b604e055ddcd02
出典データセット
uspto-grants-2014_07
特許番号
US08778950B2

反応ノート

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