tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate → HCID 67585136, compound

HRID 362031Notes

Reaction equation

HRID 362031 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]([CH2:7][S:8][C@@H:9]2[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)=[O:15])[C@H:11]([C:27](O)=[O:28])[CH2:10]2)=[CH:5][CH:4]=1.[NH2:32][C@H:33]1[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34]1>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][S:8][C@@H:9]2[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)=[O:15])[C@H:11]([C:27]([NH:32][C@H:33]3[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34]3)=[O:28])[CH2:10]2)=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylateHCID 15297071(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-proline

Product 1

HCID 67585136HCID 67585136, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

3.05 g of N,N'-carbonyldiimidazole were added to a solution of 7.99 g of (2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid in 80 ml of dry acetonitrile, and the resulting mixture was stirred at room temperature for 2 hours. At the end of this time, the reaction mixture was cooled to 0° C., after which a solution of 3.34 g of (3S)-3-amino-1-t-butoxycarbonylpyrrolidine in 30 ml of dry acetonitrile was added, and the mixture was stirred at the same temperature for 20 minutes; it was then stirred at room temperature for a further 1.4 hours and at 32° C. for 45 minutes. The reaction mixture was then concentrated by evaporation under reduced pressure, and the concentrate was diluted with 200 ml of ethyl acetate. The resulting ethyl acetate solution was washed twice with water and then once with a saturated aqueous solution of sodium chloride. The solution was then dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue was recrystallized from diethyl ether, to give 9.11 g of the title compound, as a powder.

Workup

  1. temperatureAt the end of this time, the reaction mixture was cooled to 0° C.
  2. stirringthe mixture was stirred at the same temperature for 20 minutes
  3. stirringit was then stirred at room temperature for a further 1.4 hours and at 32° C. for 45 minutes
  4. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
  5. additionthe concentrate was diluted with 200 ml of ethyl acetate
  6. washThe resulting ethyl acetate solution was washed twice with water
  7. dry with materialThe solution was then dried over anhydrous magnesium sulfate
  8. customafter which the solvent was removed by distillation under reduced pressure
  9. customThe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-1ce738225bb14f9e8a5f3deeb64af022
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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