Sodium methanethiolate → HCID 59452579, compound

HRID 419613Notes

Reaction equation

HRID 419613 reaction equation
I[CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[CH3:17][S-:18].[Na+]>CN(C=O)C.CCOC(C)=O>[CH3:17][S:18][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 9974426Tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylate

Product 1

HCID 59452579HCID 59452579, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To 1,1-dimethylethyl 4-(2-iodoethyl)-1-piperidinecarboxylate (Example 101, Step A) (23.6 g, 69.5 mmol) in DMF (100 mL) was added sodium thiomethoxide (5.37 g, 76.4 mmol). The mixture was stirred at 50° C. overnight. The mixture was diluted with EtOAc, washed with H2O (6×), dried (MgSO4), and rotovapped down to provide the title compound of Step A (17.9 g, 68.8 mmol, 99%). 1H NMR (400 MHz, CDCl3) δ 1.09 (dd, 2H), 1.44 (s, 9H), 1.53 (t, J=5.6 Hz, 3H), 1.65 (d, J=12.6 Hz, 2H), 2.08 (s, 3H), 2.51 (t, J=6.9 Hz, 2H), 2.67 (t, J=12.6 Hz, 2H), 4.06 (d, J=13.2 Hz, 2H).

Workup

  1. washwashed with H2O (6×)
  2. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-9b7c94c3ff6c4b03b37adc2423830c68
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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