1-Butanol → 5-Cyano-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide

HRID 1873519

反応式

HRID 1873519 の反応式
[CH3:1][N:2]([CH3:14])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11](=O)[CH2:12][CH:7]2[CH2:6]1)=[O:4].C1(C)C=CC(S([CH2:24][N+:25]#[C-])(=O)=O)=CC=1.CC(C)([O-])C.[K+].C(O)CCC>COCCOC.O.[Cl-].[Na+].O>[CH3:1][N:2]([CH3:14])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][CH:11]([C:24]#[N:25])[CH2:12][CH:7]2[CH2:6]1)=[O:4]

参加物

8

反応物 4

HCID 2631-ButanolHCID 161915Tosylmethyl isocyanideHCID 23665647Potassium tert-butoxideHCID 59151531N,N-Dimethyl-5-oxo-hexahydrocyclopenta[c]pyrrole-2(1H)-carboxamide

生成物 1

HCID 686261915-Cyano-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide収率 51.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

N,N-dimethyl-5-oxo-hexahydro-cyclopenta[c]pyrrole-2-carboxamide 1g (12.9 g, 0.066 mol) and 4-toluenesulfonylmethyl isocyanide (14.2 g, 0.0727 mol) were dissolved in 240 mL of 1,2-dimethoxyethane with stirring upon cooling by an ice-water bath, followed by dropwise addition of a solution of potassium tert-butoxide (14.8 g, 0.132 mol) in tent-butanol. Upon completion of the addition, the ice-water bath was removed. The reaction mixture was warmed up to room temperature and reacted overnight. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was diluted with 100 mL of water and 50 mL of saturated brine and extracted with ethyl acetate (200 mL×3). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 5-cyano-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 12a (7.0 g, yield 51%) as a light yellow oil.

後処理

  1. temperatureupon cooling by an ice-water bath
  2. additionUpon completion of the addition
  3. customthe ice-water bath was removed
  4. customreacted overnight
  5. extractionextracted with ethyl acetate (200 mL×3)
  6. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-5e5a9fc38f4b49d98e47f65eb2cea8d3
出典データセット
uspto-grants-2012_11
特許番号
US08304411B2

関連ノート

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