(R)-(+)-1-Boc-3-aminopyrrolidine → HCID 66630665, compound

HRID 2382365Notes

Reaction equation

HRID 2382365 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([NH2:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[N:15]1[CH:20]=[CH:19][C:18]([C:21](Cl)=[O:22])=[CH:17][CH:16]=1>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:21]([C:18]2[CH:19]=[CH:20][N:15]=[CH:16][CH:17]=2)=[O:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 854070(R)-(+)-1-Boc-3-aminopyrrolidineHCID 12262826Isonicotinoyl chloride hydrochloride

Product 1

HCID 66630665HCID 66630665, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A cooled (0° C.) stirred solution of (R)-3-amino-pyrrolidine-1-carboxylic acid tert-butyl ester (1.0 g, 5.36 mmol) and TEA (1.5 ml, 11.0 mmol) in THF (10 ml) is treated dropwise over 1 minute with pyridine-4 carbonyl chloride hydrochloride (0.935 g, 5.25 mmol). After 5 minutes, the reaction mixture is allowed to warm to room temperature and stirred overnight. The resulting mixture is diluted with EtOAc and washed twice with saturated sodium bicarbonate solution followed by brine. The organic portion is dried (MgSO4) and concentrated in vacuo. The crude product is purified by recrystallisation from EtOAc/iso-hexane to afford the title product. [MH+ 292].

Workup

  1. temperatureto warm to room temperature
  2. washwashed twice with saturated sodium bicarbonate solution
  3. dry with materialThe organic portion is dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by recrystallisation from EtOAc/iso-hexane

Sources & evidence

ORD record
ord-39533bc3628d43e783e4b8be28f7f157
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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