Sodium hydride → HCID 86710527, compound

HRID 341553Notes

Reaction equation

HRID 341553 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.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, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

2,2,2-Trifluoroethane-1-thiol (471 μL, 3.41 mmol) was added dropwise to a suspension of sodium hydride (60% dispersion in mineral oil, 0.065 g, 1.636 mmol) in dry DMF (10 mL) at 0 C and the mixture was stirred for 15 min. A solution of tert-butyl 4-[(methanesulfonyloxy)methyl]piperidine-1-carboxylate (prepared in an analogous manner to Intermediate 181, 1 g, 3.41 mmol) in DMF (5 mL) was added dropwise and the mixture was stirred at room temperature for 5 h. The reaction mixture was diluted with water (50 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were washed with saturated aq. sodium bicarbonate (25 mL) then brine (25 mL), dried over magnesium sulfate and concentrated under reduced pressure to provide the title compound as a light yellow oil (1.13 g, quant.). Method B HPLC-MS: MH+ requires m/z=314 Found: m/z=258 (MH+-tBu), Rt=2.39 min (98%).

Workup

  1. additionwas added dropwise
  2. stirringthe mixture was stirred at room temperature for 5 h
  3. extractionextracted with EtOAc (3×50 mL)
  4. washThe combined organic layers were washed with saturated aq. sodium bicarbonate (25 mL)
  5. dry with materialbrine (25 mL), dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-09d437709eb9477594777167d5c87d17
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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