tert-Butyl 4-bromopiperidine-1-carboxylate → tert-Butyl 4-(acetylthio)piperidine-1-carboxylate

HRID 404740Notes

Reaction equation

HRID 404740 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH:16](Br)[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]>CN(C=O)C.C(OCC)(=O)C>[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH:16]([S:3][C:1](=[O:4])[CH3:2])[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 2

HCID 15541517tert-Butyl 4-bromopiperidine-1-carboxylateHCID 23670855Potassium ethanethioate

Product 1

HCID 22494773tert-Butyl 4-(acetylthio)piperidine-1-carboxylateYield 82.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

2.2 g (19.3 mmol) Potassium thioacetate and 2.65 g (10 mmol) 4-Bromo-piperidine-1-carboxylic acid tert-butyl ester were dissolved in 50 ml of DMF and stirred at 100° C. for 4 h. The mixture was taken up in ethyl acetate and washed with brine. The organic phases were dried over Sodium sulfate and evaporated. Purification over silica gel (10% to 20% ethyl acetate in heptane) gave 2.15 g of the expected compound.

Workup

  1. washwashed with brine
  2. dry with materialThe organic phases were dried over Sodium sulfate
  3. customevaporated
  4. customPurification over silica gel (10% to 20% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-05a02250546e4fd5a5cb2153cf9297d0
Source dataset
uspto-grants-2014_06
Patent number
US08748614B2

Reaction notes

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