Dimethylformamide → [(R)-1-(4-Cyanophenyl)pyrrolidin-3-yl]carbamic Acid

HRID 2069326Notes

Reaction equation

HRID 2069326 reaction equation
C(OC(N[N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)=O)(C)(C)C.F[C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1.[C:23](=[O:26])([O-])[O-:24].[Cs+].[Cs+].C[N:30](C=O)C>O.C(OCC)(=O)C>[C:19]([C:18]1[CH:21]=[CH:22][C:15]([N:9]2[CH2:10][CH2:11][C@@H:12]([NH:30][C:23](=[O:26])[OH:24])[CH2:13]2)=[CH:16][CH:17]=1)#[N:20]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 145174-FluorobenzonitrileHCID 21959621Tert-butyl pyrrolidin-1-ylcarbamate

Product 1

HCID 68574711[(R)-1-(4-Cyanophenyl)pyrrolidin-3-yl]carbamic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (3R)-(+)-(tert-butoxycarbonylaminopyrrolidine (1.0 g), p-fluorobenzonitrile (650 mg), cesium carbonate (1.75 g) and 5 ml of DMF was stirred at 50° C. for 12 h. Ethyl acetate and water were then added to the reaction solution, and the organic phase was washed twice with water, dried over sodium sulfate and filtered, and the solvent was removed in vacuo. The residue was purified by preparative HPLC. The product with the molecular weight of 287.36 (C16H21N3O2) was obtained in this way; MS (ESI): 288.20 (M+H+).

Workup

  1. washthe organic phase was washed twice with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified by preparative HPLC
  6. customThe product with the molecular weight of 287.36 (C16H21N3O2) was obtained in this way

Sources & evidence

ORD record
ord-e154934c1987442daa518fd3d6571095
Source dataset
uspto-grants-2012_10
Patent number
US08299104B2

Reaction notes

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