Sodium methanethiolate → HCID 68517449, compound

HRID 1948342Notes

Reaction equation

HRID 1948342 reaction equation
[CH3:1][S-:2].[Na+].Br[CH:5]1[C:10](=[O:11])[CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6]1>C1COCC1>[CH3:1][S:2][CH:5]1[C:10](=[O:11])[CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6]1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 106839701-tert-Butyloxycarbonyl-3-bromo-4-oxopiperidine2×

Product 1

HCID 68517449HCID 68517449, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium thiomethoxide (805 mg, 11.5 mmol) was added to a solution of tert-butyl 3-bromo-4-oxopiperidine-1-carboxylate (Intermediate 182, 3.20 g, 11.5 mmol) and THF (15 ml) at 0° C. The resultant mixture was allowed to slowly warm to room temperature and stirred overnight. The reaction was quenched with water (15 ml) and diluted with ethyl acetate (150 ml). The organic phase was separated and washed with brine. The combined aqueous phase was back extracted with ethyl acetate (50 ml). The combined organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography (hexanes/ethyl acetate, 7:1) to provide the title compound (2.4 g).

Workup

  1. customThe reaction was quenched with water (15 ml)
  2. additiondiluted with ethyl acetate (150 ml)
  3. customThe organic phase was separated
  4. washwashed with brine
  5. extractionThe combined aqueous phase was back extracted with ethyl acetate (50 ml)
  6. dry with materialThe combined organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude residue was purified by flash chromatography (hexanes/ethyl acetate, 7:1)

Sources & evidence

ORD record
ord-e36836f74c3d41bc91c2d704a0e40a9a
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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