Lawesson's reagent → tert-Butyl (2S)-2-carbamothioylpyrrolidine-1-carboxylate

HRID 1963973Notes

Reaction equation

HRID 1963973 reaction equation
[C:1]([C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])(=O)[NH2:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:25])=CC=1>C1COCC1>[C:1]([C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])(=[S:25])[NH2:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 7019053tert-butyl (S)-2-carbamoylpyrrolidine-1-carboxylate2×

Product 1

HCID 54006182tert-Butyl (2S)-2-carbamothioylpyrrolidine-1-carboxylateYield 83.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A round-bottomed flask with (S)-tert-butyl 2-carbamoylpyrrolidine-1-carboxylate (compound 10a, 3.0 g, 14.0 mmol) and Lawesson's reagent (6.8 g, 16.8 mmol) was flushed with nitrogen. Dry THF (40 ml) was added as the solvent. The reaction mixture was stirred at 70° C. under nitrogen for 8 hours. After cooled to room temperature, the resulting mixture was evaporated under reduced pressure and purified by column chromatography (ethyl acetate:n-hexane=1:2) to yield pure product 11a (2.7 g).

Workup

  1. temperatureAfter cooled to room temperature
  2. customthe resulting mixture was evaporated under reduced pressure
  3. custompurified by column chromatography (ethyl acetate:n-hexane=1:2)

Sources & evidence

ORD record
ord-bad9d92e94294b58b5891e4c6637f2c9
Source dataset
uspto-grants-2013_04
Patent number
US08415482B2

Reaction notes

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