Water → 1-t-Butoxycarbonyl-3-dibenzylamino-4-methoxypyrrolidine

HRID 358898Notes

Reaction equation

HRID 358898 reaction equation
[H-].[Na+].[CH3:3]I.[C:5]([O:9][C:10]([N:12]1[CH2:16][CH:15]([OH:17])[CH:14]([N:18]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].O>O1CCCC1>[C:5]([O:9][C:10]([N:12]1[CH2:16][CH:15]([O:17][CH3:3])[CH:14]([N:18]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:13]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 200671491-t-Butoxycarbonyl-3-dibenzylamino-4-hydroxypyrrolidine

Product 1

HCID 200671541-t-Butoxycarbonyl-3-dibenzylamino-4-methoxypyrrolidineYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.19 g (0.0047 mole) of sodium hydride (as a 60% w/w dispersion in mineral oil) and 0.89 g (0.0063 mole) of methyl iodide were added, in that order, to a solution of 1.2 g (0.0031 mole) of 1-t-butoxycarbonyl-3-dibenzylamino-4-hydroxypyrrolidine [prepared as described in Step (1) above] dissolved in 10 ml of tetrahydrofuran. The mixture was then stirred at room temperature for 5 hours. At the end of this time, water was added to the reaction mixture, which was then extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried and concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through silica gel, eluted with a 5:95 by volume mixture of ethyl acetate and toluene, to give 0.99 g of 1-t-butoxycarbonyl-3-dibenzylamino-4-methoxypyrrolidine as a colorless oil.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washwas washed with water
  4. customdried
  5. concentrationconcentrated by evaporation under reduced pressure
  6. washeluted with a 5:95 by volume mixture of ethyl acetate and toluene

Sources & evidence

ORD record
ord-04f769001bab4f64ade66d45a0e6d28c
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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