Benzaldehyde → HCID 53768433, compound

HRID 344439Notes

Reaction equation

HRID 344439 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][NH2:19])[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[BH4-].[Na+].O>C(O)C>[CH2:20]([NH:19][CH2:18][CH2:17][CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][CH:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:11]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 962WaterHCID 4311764Sodium borohydrideHCID 53780052HCID 53780052, compound

Product 1

HCID 53768433HCID 53768433, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(3-tert-butoxycarbonylaminomethylpyrrolidin-1-yl)-butylamine (2.0 g) and benzaldehyde (0.86 g) in ethanol (50 ml) was stirred at 70° C. for 3 hr. After cooling, sodium borohydride was added, and the mixture was stirred at room temperature for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 1.74 g of N-benzyl-4-(3-tert-butoxycarbonylaminomethylpyrrolidin-1-yl)butylamine.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4d024c7387ca4a5aacae1abbc850e034
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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