Sodium Bicarbonate → N-Boc-pyrrolidine

HRID 2039071Notes

Reaction equation

HRID 2039071 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1C1NC(Br)=CN=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+]>O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 56605248tert-Butyl 2-(5-bromo-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 643455N-Boc-pyrrolidineYield 76.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

2,6-(bis-pinocolato)diboranonaphthalene (0.501 g), 2-(5-bromo-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.885 g), and NaHCO3 (0.562 g) were dissolved in a mixture of 1,2-dimethoxyethanedichloromethane (15 mL) and water (5 mL). The solution was degassed with nitrogen, and Pd(PPh3)4 (0.0935 g) was added. The reaction mixture was stirred at 90° C. for 16 hours and evaporated under vacuum. Solid was dissolved in DCM (20 mL) and extracted twice with water and once with brine. Solution was evaporated, recrystallized from ethyl acetate, and dried under vacuum, giving 2-(5-{6-[2-(1′-carboxylic acid tert-butyl ester-pyrrolidin-2-yl)-3H-imidazol-4-yl]-naphthalen-2-yl}-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.365 g, 46%) as a white solid.

Workup

  1. customThe solution was degassed with nitrogen, and Pd(PPh3)4 (0.0935 g)
  2. additionwas added
  3. customevaporated under vacuum
  4. dissolutionSolid was dissolved in DCM (20 mL)
  5. extractionextracted twice with water and once with brine
  6. customSolution was evaporated
  7. customrecrystallized from ethyl acetate
  8. customdried under vacuum

Sources & evidence

ORD record
ord-dc5fe96c0d264044a0eb5dd8019353f9
Source dataset
uspto-grants-2013_11
Patent number
US08575118B2

Reaction notes

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