Water → HCID 14555451, compound

HRID 1655639Notes

Reaction equation

HRID 1655639 reaction equation
C([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14](=[O:25])[C@@H:15]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH3:16])[CH2:9]1)C1C=CC=CC=1.O.[H][H]>CO.[OH-].[OH-].[Pd+2]>[C:21]([O:20][C:18]([NH:17][C@@H:15]([CH3:16])[C:14]([NH:13][C@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)=[O:25])=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

6

Reactant 3

HCID 962WaterHCID 22847908HCID 22847908, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14555451HCID 14555451, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

1 Benzyl-3-(S)-[2-(S)-(tert-butoxycarbonylamino)propionylamino]pyrrolidine (21.3 g) was dissolved in methanol (250 mL), and hydrogenated over 20% palladium hydroxide on charcoal, 50% water wet (5.0 g) at 50 psig and 25° to 40° C. until the uptake of hydrogen ceased. The reaction was then filtered through celite to remove the catalyst and the residue rinsed with methanol (100 mL) and the combined filtrates concentrated under vacuum to give 3-(S)-[2-(S)-(tert-butoxycarbonylamino)propionylamino]pyrrolidine (14.6 g) as a colorless oil which crystallized on standing: HPLC: 99% S,S isomer. A portion was recrystallized from methyl tert-butyl ether: mp 137°-138° C.

Workup

  1. customat 50 psig and 25° to 40° C.
  2. filtrationThe reaction was then filtered through celite
  3. customto remove the catalyst
  4. washthe residue rinsed with methanol (100 mL)
  5. concentrationthe combined filtrates concentrated under vacuum

Sources & evidence

ORD record
ord-a1e19305b9da4e64bfc08b8f26c2666a
Source dataset
uspto-grants-1993_10
Patent number
US05250704

Reaction notes

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