Ethylamine → HCID 59859923, compound

HRID 1959423Notes

Reaction equation

HRID 1959423 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(O[N:24]1N=N[C:26]2C=CC=N[C:25]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N)C.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH2:25]([NH:24][C:13]([C@H:9]1[CH2:10][CH2:11][CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:15])[CH3:26]

Participants

7

Reactant 4

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 59859923HCID 59859923, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R)-1-tert-butoxycarbonylpyrrolidine-2-carboxylic acid (810 mg, 3.8 mmol) and HATU (1.40 g, 3.8 mmol) in DMF (7.5 mL) was added ethanamine (3.8 mL of 2 M, 7.5 mmol) followed by DIEA (1.0 g, 1.4 mL, 8.0 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with EtOAc and washed sequentially with 1M HCl, saturated NaHCO3 and brine solution. The organic layer was dried (Na2SO4) filtered and concentrated under reduced pressure to obtain tert-butyl (2R)-2-(ethylcarbamoyl)pyrrolidine-1-carboxylate (624 mg, 68%). LC/MS m/z 243.4 [M+H]+.

Workup

  1. washwashed sequentially with 1M HCl, saturated NaHCO3 and brine solution
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-49d889727b9e4e71b124128510ccfeb4
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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