Lawesson's reagent → Tert-butyl 4-(carbamothioylmethoxy)piperidine-1-carboxylate

HRID 221347Notes

Reaction equation

HRID 221347 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][C:16](=O)[NH2:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1>C(COC)OC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][C:16](=[S:28])[NH2:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 578567294-Carbamoylmethoxypiperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 45496681Tert-butyl 4-(carbamothioylmethoxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 4-carbamoylmethoxypiperidine-1-carboxylic acid tert-butyl ester (Preparation 13, 67.5 mg, 260 μmol) and Lawesson's reagent (116 mg, 287 μmol) in dimethoxyethane (1.5 ml) was stirred at rt for 24 h. The solvent was evaporated and the residue purified by flash chromatography (5% MeOH in CH2Cl2) to afford the title compound: δH (CDCl3) 1.50 (9H, s), 1.55-1.63 (2H, m), 1.88-1.95 (2H, m), 3.12 (2H, ddd), 3.59-3.66 (1H, m), 3.79-3.87 (2H, m), 4.40, (2H, s), 7.65 (1H, bs), 8.04 (1H, bs).

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by flash chromatography (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-3d4372f7ce8b4377a965f1e7106faa8b
Source dataset
uspto-grants-2012_06
Patent number
US08207147B2

Reaction notes

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