Sodium 2-propanethiolate → HCID 86710528, compound

HRID 341547Notes

Reaction equation

HRID 341547 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][CH:20]([S-:22])[CH3:21].[Na+]>CN(C=O)C.CCOC(C)=O>[CH3:19][CH:20]([S:22][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)[CH3:21]

Participants

5

Reactant 2

HCID 3470666Sodium 2-propanethiolateHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine2×

Product 1

HCID 86710528HCID 86710528, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 4-(methanesulfonyloxy)piperidine-1-carboxylate (Intermediate 239, 0.320 g, 1.15 mmol) and sodium 2-propanethiolate (0.147 g, 1.50 mmol) were combined in DMF (3 mL) and stirred at room temperature for 18 h. The mixture was then diluted with EtOAc (30 mL) and washed with water (3×10 mL). The organic layer was dried over sodium sulfate and concentrated to yield a yellow oil. This was purified by FCC, eluting with a gradient of 0-20% EtOAc in heptane to afford the title compound as a colourless oil (0.179 g, 60%). 1H NMR (500 MHZ, CDCl3) δ ppm 3.88 (2H, br s), 2.94 (1H, m), 2.86 (2H, m), 2.77 (1H, m), 1.83 (2H, d), 1.42 (2H, m), 1.38 (9H, s) and 1.20 (6H, d).

Workup

  1. washwashed with water (3×10 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customto yield a yellow oil
  5. customThis was purified by FCC
  6. washeluting with a gradient of 0-20% EtOAc in heptane

Sources & evidence

ORD record
ord-14afaffc19194924a41410fe9291060e
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

Loading…