Ethylamine → HCID 68078873, compound

HRID 1959426Notes

Reaction equation

HRID 1959426 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][C:14]([N:16]2[CH:20]=[CH:19]N=C2)=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N)C.CCN(C(C)C)C(C)C>C1COCC1.CCOC(C)=O>[CH2:20]([NH:16][C:14]([O:13][C@H:10]1[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:9]1)=[O:15])[CH3:19]

Participants

6

Reactant 3

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 66744440HCID 66744440, compound

Product 1

HCID 68078873HCID 68078873, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of [(35)-1-tert-butoxycarbonylpyrrolidin-3-yl]imidazole-1-carboxylate (173 mg, 0.61 mmol) in THF (2.5 mL) at room temperature under an atmosphere of nitrogen was added a solution of ethanamine (369 mg, 461 μL of 2 M, 0.9 mmol) in THF followed by the addition of DIEA (119 mg, 161 μL, 0.9 mmol). The reaction mixture was heated at 60° C. for 1.5 h, cooled to room temperature and diluted with EtOAc. The organic layer was washed with 5 mL of 1M HCl solution, dried over MgSO4, filtered and concentrated under reduced pressure to obtain tert-butyl (35)-3-(ethylcarbamoyloxy)pyrrolidine-1-carboxylate. LC/MS m/z 259.2 [M+H]+.

Workup

  1. temperaturecooled to room temperature
  2. washThe organic layer was washed with 5 mL of 1M HCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eccc5eee8ed040768b7f4a1892a4f0bf
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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