Sodium borohydride → 1-(4-Chlorophenyl)-3-(hydroxymethyl)pyrrolidin-2-one

HRID 1740378ノート

反応式

HRID 1740378 の反応式
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][CH:12]([C:15](OCC)=[O:16])[C:11]2=[O:20])=[CH:6][CH:5]=1.[Cl-].[Ca+2].[Cl-]>CO>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][CH:12]([CH2:15][OH:16])[C:11]2=[O:20])=[CH:6][CH:5]=1

参加物

5

反応物 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 18544410Ethyl 1-(4-chlorophenyl)-2-oxopyrrolidine-3-carboxylate

生成物 1

HCID 218386441-(4-Chlorophenyl)-3-(hydroxymethyl)pyrrolidin-2-one収率 92.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Under ice-cooling, 3.9 g of sodium borohydride was added portionwise to a solution of 30.0 g of 1-(4-chlorophenyl)-3-ethoxycarbonyl-2-pyrrolidinone and 15 g of anhydrous calcium chloride in 150 mL of methanol. After completion of the reaction, the mixture was concentrated, and water and ethyl acetate were added. The mixture was acidified with diluted hydrochloric acid. After separation, the organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was crystallized with n-hexane-ethyl ether. The crystals were collected by filtration, washed with a mixture of n-hexane and diethyl ether and dried in vacuo to give 23.3 g of the title compound.

後処理

  1. temperatureUnder ice-cooling
  2. customAfter completion of the reaction
  3. concentrationthe mixture was concentrated
  4. additionwater and ethyl acetate were added
  5. customAfter separation
  6. washthe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was crystallized with n-hexane-ethyl ether
  10. filtrationThe crystals were collected by filtration
  11. washwashed with a mixture of n-hexane and diethyl ether
  12. customdried in vacuo

出典と根拠

ORDレコード
ord-ff482b211dcf4abfad68e6fd86be85cd
出典データセット
uspto-grants-1999_10
特許番号
US05969138

反応ノート

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