Isobutyraldehyde → HCID 59717692, compound

HRID 2224643Notes

Reaction equation

HRID 2224643 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:14](=O)[CH:15]([CH3:17])[CH3:16].[H][H]>C(O)C.[Pd]>[CH2:14]([NH:13][C@H:10]1[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9]1)[CH:15]([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 6561IsobutyraldehydeHCID 27563701-Boc-3-aminopyrrolidineHCID 178418361HCID 178418361, compound

Product 1

HCID 59717692HCID 59717692, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-Amino-pyrrolidine-1-carboxylic acid tert-butyl ester (3 g, 16.1 mmol) was added to a solution of isobutyraldehyde (1.61 mL, 17.7 mmol) and 10% Pd/C (360 mg) in ethanol (60 mL) and the reaction mixture left under about 415 kPa (about 60 psi) of hydrogen gas for 18 hours. The reaction mixture was filtered through Arbocel®, washing through thoroughly with ethyl acetate. The filtrate was concentrated in vacuo and the crude product purified by column chromatography on silica gel eluting with ethyl acetate:pentane 1:1 to yield the title product, 2.8 g, (73%).

Workup

  1. filtrationThe reaction mixture was filtered through Arbocel®
  2. washwashing through thoroughly with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe crude product purified by column chromatography on silica gel eluting with ethyl acetate:pentane 1:1

Sources & evidence

ORD record
ord-6e142ce1d6134e18a224b7bbb62ef87f
Source dataset
uspto-grants-2008_05
Patent number
US07378436B2

Reaction notes

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