Sodium borohydride → 1-Benzylideneamino-3-propyl-5-hydroxyhexahydrocylopenta[d]imidazol-2(1H)-one

HRID 1885898ノート

反応式

HRID 1885898 の反応式
[CH:1](=[N:8][N:9]1[CH:13]2[CH2:14][C:15](=[O:17])[CH2:16][CH:12]2[N:11]([CH2:18][CH2:19][CH3:20])[C:10]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH:1](=[N:8][N:9]1[CH:13]2[CH2:14][CH:15]([OH:17])[CH2:16][CH:12]2[N:11]([CH2:18][CH2:19][CH3:20])[C:10]1=[O:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 544413591-Benzylideneamino-3-propyltetrahydrocyclopenta[d]imidazol-2,5(1H,3H)-dione

生成物 1

HCID 679048761-Benzylideneamino-3-propyl-5-hydroxyhexahydrocylopenta[d]imidazol-2(1H)-one収率 35.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

The compound of step (e) (21 g) was dissolved in methanol (100 ml) and the solution cooled to 0° C. while sodium borohydride (1.5 g) was added portionwise over 15 minutes. When addition was complete, the solvent was removed in vacuo, water (100 ml) and chloroform (100 ml) added and the organic phase separated. After drying over anhy. sodium sulphate, filtration and concentration in vacuo gave the crude product as a brown gum (21 g). This was purified by column chromatography (silica, 10:1 diethyl ether:methanol) to give the desired product as fine white needles (7.5 g), mp 150.3°-150.8° C.

後処理

  1. additionwas added portionwise over 15 minutes
  2. additionWhen addition
  3. customthe solvent was removed in vacuo, water (100 ml) and chloroform (100 ml)
  4. additionadded
  5. customthe organic phase separated
  6. customAfter drying over anhy
  7. filtrationsodium sulphate, filtration and concentration in vacuo
  8. customgave the crude product as a brown gum (21 g)
  9. customThis was purified by column chromatography (silica, 10:1 diethyl ether:methanol)

出典と根拠

ORDレコード
ord-988e1e2df84242999737c7cb204e68d6
出典データセット
uspto-grants-1992_09
特許番号
US05147885

反応ノート

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