tert-Butanol → 1-Benzyl-3-(tert-butoxycarbonylamino)pyrrolidine

HRID 555356Notes

Reaction equation

HRID 555356 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C)(C)C.[C:19]([O:23][C:24](OC([O-])=O)=[O:25])([CH3:22])([CH3:21])[CH3:20]>[OH-].[Na+]>[C:19]([O:23][C:24](=[O:25])[NH:13][CH:10]1[CH2:11][CH2:12][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9]1)([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 27566131-Benzyl-3-aminopyrrolidineHCID 22064466Tert-butyldicarbonate

Product 1

HCID 35758231-Benzyl-3-(tert-butoxycarbonylamino)pyrrolidineYield 97%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

1-benzylpyrrolidin-3-ylamine (10 g, 57 mmol) was dissolved in 3M aqueous sodium hydroxide solution (21 ml) and t-butanol (114 ml) in a 500 ml vessel, and t-butyl-dicarbonate ((t-Boc)2O; 13.07 g, 59.9 mmol) was added thereto while stirring. The resulting mixture was reacted for 12 hrs. After the completion of the reaction, the reaction product was extracted with ethyl acetate twice. The organic layer was separated, washed with 0.1N hydrochloric acid solution and brine in order, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue thus obtained was subjected to a silica gel column chromatography to obtain 15.25 g of the title compound as a white solid (yield 97%).

Workup

  1. customThe resulting mixture was reacted for 12 hrs
  2. customAfter the completion of the reaction
  3. extractionthe reaction product was extracted with ethyl acetate twice
  4. customThe organic layer was separated
  5. washwashed with 0.1N hydrochloric acid solution and brine in order
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue thus obtained

Sources & evidence

ORD record
ord-7a1759dcfe6847079533f3fe123c503c
Source dataset
uspto-grants-2011_11
Patent number
US08053435B2

Reaction notes

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