Lawesson's reagent → tert-Butyl (2R)-2-carbamothioylpiperidine-1-carboxylate

HRID 1664691Notes

Reaction equation

HRID 1664691 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[C:14](=O)[NH2:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[C:14](=[S:26])[NH2:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 7145549tert-Butyl (2R)-2-carbamoylpiperidine-1-carboxylate

Product 1

HCID 59860523tert-Butyl (2R)-2-carbamothioylpiperidine-1-carboxylateYield 100.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (R)-2-carbamoyl-piperidine-1-carboxylic acid tert-butyl ester (1.31 g, 6 mmol) in dioxane (20 mL) was treated under argon with Lawesson's reagent (1.16 g, 3 mmol). The mixture was stirred at room temperature overnight. The volatiles were evaporated and the resulting white solid purified by flash chromatography (heptane/ethyl acetate gradient) to yield (R)-2-thiocarbamoyl-piperidine-1-carboxylic acid tert-butyl ester as a white solid (0.74 g, 47%), MS (ISP): 245.4 (M+H)+..

Workup

  1. customThe volatiles were evaporated
  2. customthe resulting white solid purified by flash chromatography (heptane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-c162657339954d7eb9f2d115a02f2160
Source dataset
uspto-grants-2011_10
Patent number
US08039487B2

Reaction notes

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