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

HRID 1885898노트

반응식

HRID 1885898 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-988e1e2df84242999737c7cb204e68d6
출처 데이터셋
uspto-grants-1992_09
특허 번호
US05147885

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