Dibenzylamine → 1-t-Butoxycarbonyl-3-dibenzylamino-4-hydroxypyrrolidine

HRID 358897Notes

Reaction equation

HRID 358897 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]2[O:13][CH:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:14]([NH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([OH:13])[CH:11]([N:21]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:12]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 7656DibenzylamineHCID 10103880tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

Product 1

HCID 200671491-t-Butoxycarbonyl-3-dibenzylamino-4-hydroxypyrrolidineYield 15.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.7 g (0.02 mole) of 1-t-butoxycarbonyl-3,4-epoxypyrrolidine (prepared as described in Preparation 8) were dissolved in 15 ml of ethanol. 7.88 g (0.04 mole) of dibenzylamine were added to the solution, and the mixture was heated under reflux for 10 hours. At the end of this time, the solvent was removed by evaporation under reduced pressure, and the residue was subjected to column chromatography through silica gel, eluted with a 12:88 by volume mixture of ethyl acetate and toluene, to give 1.21 g of 1-t-butoxycarbonyl-3-dibenzylamino-4-hydroxypyrrolidine as a pale yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 10 hours
  3. customAt the end of this time, the solvent was removed by evaporation under reduced pressure
  4. washeluted with a 12:88 by volume mixture of ethyl acetate and toluene

Sources & evidence

ORD record
ord-5a390b09771547ce95524fad9834a624
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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