Potassium Carbonate → HCID 67241454, compound

HRID 1949587Notes

Reaction equation

HRID 1949587 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].Br[CH:15]([CH3:19])[C:16]([NH2:18])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CC#N>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][CH:15]([C:16](=[O:17])[NH2:18])[CH3:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1011182-BromopropanamideHCID 27563701-Boc-3-aminopyrrolidine

Product 1

HCID 67241454HCID 67241454, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of MeCN (3 mL) was added 3-Amino-pyrrolidine-1-carboxylic acid tert-butyl ester (0.186 g, 1 mmol), 2-Bromo-propionamide (0.15 g, 1 mmol) and potassium carbonate (0.153 g, 1.1 mmol). The resulting mixture was heated at 80° C. overnight and partitioned between dichloromethane and water. The combined organic extracts were washed with brine, dried, and evaporated. The residue was purified by flash column chromatography on silica gel, eluting with MeOH/CH2Cl2 (20/80) to afford the title product.

Workup

  1. custompartitioned between dichloromethane and water
  2. washThe combined organic extracts were washed with brine
  3. customdried
  4. customevaporated
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with MeOH/CH2Cl2 (20/80)

Sources & evidence

ORD record
ord-c401a708670e4b0db7c2ce65c36a060b
Source dataset
uspto-grants-2013_03
Patent number
US08399681B2

Reaction notes

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