Water → Tert-butyl (1-(4-methylpyridin-2-yl)pyrrolidin-3-yl)carbamate

HRID 1059893Notes

Reaction equation

HRID 1059893 reaction equation
F[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[C:9]([O:13][C:14]([NH:16][CH:17]1[CH2:21][CH2:20][NH:19][CH2:18]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([N:19]2[CH2:20][CH2:21][CH:17]([NH:16][C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15])[CH2:18]2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27374032-Fluoro-4-methylpyridineHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamate

Product 1

HCID 18667607Tert-butyl (1-(4-methylpyridin-2-yl)pyrrolidin-3-yl)carbamateYield 54.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 2-fluoro-4-methylpyridine (1.11 g), 3-(tert-butoxycarbonylamino)pyrrolidine (1.68 g) and potassium carbonate (1.49 g) in N,N-dimethylformamide (20 ml) was stirred at 100° C. for 16 hours. After cooling, the mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water five times and brine, dried over sodium sulfate and evaporated under reduced pressure to give 1-(4-methylpyridin-2-yl)-3-(tert-butoxycarbonylamino)pyrrolidine (1.36 g).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water five times and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9762b506dcbf498abef31fa08e845d4f
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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