Benzyl succinimido carbonate → 1-Cbz-3-Boc-Amino pyrrolidine

HRID 1970475Notes

Reaction equation

HRID 1970475 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].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>[CH2:19]([O:26][C:27]([N:11]1[CH2:12][CH2:13][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:10]1)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 83172Benzyl succinimido carbonateHCID 516892Sodium BicarbonateHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamate

Product 1

HCID 145554781-Cbz-3-Boc-Amino pyrrolidine

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 2.05 g 3-(tert-butoxycarbonylamino)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-19049a96847c4c92964fa3a7fab2ea36
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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