Pyridine → HCID 86707398, compound

HRID 338827

Reaction equation

HRID 338827 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@:13]([CH3:19])([C:16](O)=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.[N:35]1C=CC=CC=1.[NH4+].[OH-].O>C(OCC)(=O)C.O>[C:16]([C@@:13]1([CH3:19])[CH2:14][CH2:15][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:12]1)(=[O:17])[NH2:35]

Participants

7

Reactant 4

HCID 1049PyridineHCID 90495Di-tert-butyl dicarbonateHCID 76853756(S)-1-((benzyloxy)carbonyl)-3-methylpyrrolidine-3-carboxylic acidHCID 86589665Water ammonium hydroxide

Product 1

HCID 86707398HCID 86707398, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (S)-1-(benzyloxycarbonyl)-3-methylpyrrolidine-3-carboxylic acid (32.87 g, 124.8 mmol), Boc2O (29.97 g, 137.3 mmol) in ethyl acetate (200 mL) was added pyridine (12.62 mL, 156.1 mmol) and the reaction mixture was stirred at ambient temperature for 3 hours. A solution of 28-30% w/w NH4OH/water (21.79 mL, 162.3 mmol) was added. The reaction was stirred at ambient temperature for 5 hours. Water (50 mL) was added. The organic layer was separated, washed with 1N HCl (50 mL) and brine, dried and concentrated under reduced pressure to give (S)-benzyl 3-carbamoyl-3-methylpyrrolidine-1-carboxylate (31.30 g, 119.3 mmol, 95.6% yield) as an oil.

Workup

  1. stirringThe reaction was stirred at ambient temperature for 5 hours
  2. customThe organic layer was separated
  3. washwashed with 1N HCl (50 mL) and brine
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a151995ce2644fc89a3d897ae133fc4c
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Linked notes

Loading…