Lawesson's reagent → tert-butyl (2R)-2-carbamothioylpyrrolidine-1-carboxylate

HRID 1752291Notes

Reaction equation

HRID 1752291 reaction equation
[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@@H:9]1[C:10]([NH2:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:25])=CC=1>C(Cl)Cl>[C:10]([C@H:9]1[CH2:13][CH2:14][CH2:15][N:8]1[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])(=[S:25])[NH2:12]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 2756826D-1-N-Boc-prolinamide

Product 1

HCID 14019689tert-butyl (2R)-2-carbamothioylpyrrolidine-1-carboxylateYield 170.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution Boc-D-prolinamide (2.63 g, 12.3 mmol) in CH2Cl2 (25 mL) at rt was added Lawesson's reagent (2.73 g, 6.75 mmol). The mixture was stirred overnight and concentrated. The oily residue was purified by chromatography on a 40-g silica gel cartridge, eluted with a 0-20% MeOH in CH2Cl2 gradient, to afford (R)-tert-butyl 2-carbamothioylpyrrolidine-1-carboxylate (2.65 g, 94%) as a tan solid. LC-MS Method 1 tR=1.23 min, m/z=231, 173, 131.

Workup

  1. concentrationconcentrated
  2. customThe oily residue was purified by chromatography on a 40-g silica gel cartridge
  3. washeluted with a 0-20% MeOH in CH2Cl2 gradient

Sources & evidence

ORD record
ord-3e6ed10efe08432e9a524b049020c7fa
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Reaction notes

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