Sodium hydride → HCID 86710527, compound

HRID 341513Notes

Reaction equation

HRID 341513 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][SH:4].[H-].[Na+].CS(O[CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)(=O)=O>CN(C=O)C.CCOC(C)=O>[F:1][C:2]([F:6])([F:5])[CH2:3][S:4][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 2765838Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate2×HCID 41339242,2,2-Trifluoroethanethiol

Product 1

HCID 86710527HCID 86710527, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2,2,2-Trifluoroethane-1-thiol (0.151 mL, 1.636 mmol) was added dropwise to a suspension of sodium hydride (60% dispersion in mineral oil, 0.065 g, 1.636 mmol) in anhydrous DMF (3 mL) at 0 C. A solution of tert-butyl 4-[(methanesulfonyloxy)methyl]piperidine-1-carboxylate (Intermediate 181, 0.320 g, 1.091 mmol) in DMF (4 mL) was then added dropwise and the reaction mixture was stirred at room temperature for 4 h. The mixture was diluted with EtOAc (30 mL) and washed with a saturated aqueous solution of sodium bicarbonate (10 mL) followed by brine (10 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude material was purified by FCC (EtOAc: heptane, 20:80) to provide the title compound as a colourless oil (0.288 g, 82%). Method B HPLC-MS: MH+ requires m/z=313 Found: m/z=257 (M minus tert-butyl), Rt=2.28 min (97%).

Workup

  1. washwashed with a saturated aqueous solution of sodium bicarbonate (10 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe crude material was purified by FCC (EtOAc: heptane, 20:80)

Sources & evidence

ORD record
ord-8ac7cb1e99974927aca4e1a07e6493c0
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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