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

HRID 1885898Notes

Reaction equation

HRID 1885898 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-988e1e2df84242999737c7cb204e68d6
Source dataset
uspto-grants-1992_09
Patent number
US05147885

Reaction notes

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