Water → Tert-butyl 4-(methylthio)piperidine-1-carboxylate

HRID 1813990Notes

Reaction equation

HRID 1813990 reaction equation
CS(O[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)(=O)=O.[CH3:19][S-:20].[Na+].O>CN(C)C=O>[CH3:19][S:20][CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 4378561Sodium methanethiolate

Product 1

HCID 11053478Tert-butyl 4-(methylthio)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl 4-[(methylsulfonyl)oxy]piperidine-1-carboxylate 5-2 (27.060 g, 96.87 mmol) was dissolved in 150 mL DMF (dimethylformamide). Sodium thiomethoxide (13.579 g, 193.73 mmol) was added and the solution was heated to 80° C. for 17 hours. The solution was allowed to cool to room temperture. The reaction was then poured into 200 mL H2O and was extracted with ether (4×). The combined organic layers were dried (Na2SO4), filtered, and concentrated to afford tert-butyl 4-(methylthio)piperidine-1-carboxylate 5-3 as a yellow oil. 1H NMR (CDCl3) δ 4.01 (bs, 2H), 3.92 (m, 1H), 3.49 (m, 1H), 2.89 (m, 2H), 2.67 (m, 1H), 2.10 (s, 3H), 1.95-1.89 (m, 2H), 1.46 (s, 9H).

Workup

  1. temperatureto cool to room temperture
  2. extractionwas extracted with ether (4×)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e7380e86a2134d16aed281f564476b31
Source dataset
uspto-grants-2005_04
Patent number
US06875767B2

Reaction notes

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