Benzyl succinimido carbonate → 1-Boc-3-Cbz-Aminopyrrolidine

HRID 1970470Notes

Reaction equation

HRID 1970470 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.C([O-])(O)=O.[Na+].[CH2:19]([O:26][C:27](ON1C(=O)CCC1=O)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCOCC1.O.C(OCC)(=O)C>[C:10]([O:9][C:7]([N:4]1[CH2:5][CH2:6][CH:2]([NH:1][C:27]([O:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:28])[CH2:3]1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 83172Benzyl succinimido carbonateHCID 516892Sodium BicarbonateHCID 27563701-Boc-3-aminopyrrolidine

Product 1

HCID 105436911-Boc-3-Cbz-Aminopyrrolidine

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A mixture of 2.05 g 3-amino-1-N-Boc-pyrrolidine, 1.85 g NaHCO3 and 3.17 g N-(Benzyloxycarbonyloxy)succinimide in 10 ml dioxane/water 1:1 was stirred for 12 h at RT. The reaction mixture was diluted with ethyl acetate, the phases separated and the organic phase washed with saturated NaHCO3 and brine. The crude product obtained after evaporation of the solvent was used in the next reaction step without further purification.

Workup

  1. customthe phases separated
  2. washthe organic phase washed with saturated NaHCO3 and brine

Sources & evidence

ORD record
ord-b1690fc041dd48a0bf1676e19c1663a1
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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