(Diethylamino)sulfur trifluoride → Tert-butyl 4-[1-fluoro-3-(6-methylpyridin-2-yl)prop-2-yn-1-yl]piperidine-1-carboxylate

HRID 1896002Notes

Reaction equation

HRID 1896002 reaction equation
O[CH:2]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[N:6]=1.C(N(S(F)(F)[F:31])CC)C>C(Cl)Cl>[F:31][CH:2]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[N:6]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 68725592Tert-butyl 4-[1-hydroxy-3-(6-methylpyridin-2-yl)prop-2-ynyl]piperidine-1-carboxylate

Product 1

HCID 25181654Tert-butyl 4-[1-fluoro-3-(6-methylpyridin-2-yl)prop-2-yn-1-yl]piperidine-1-carboxylateYield 46.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a solution of the Compound of Example 39 (300 mg, 0.91 mmol) in anhydrous CH2Cl2 (10 mL) cooled at −78° C. was dropped diethylaminosulfur trifluoride (144 μL, 1.01 mmol). The reaction mixture was kept at the same temperature for 2 h, then warmed up to r.t., quenched with water and extracted with CH2Cl2. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with Petroleum Ether-EtOAc 7:3, affording the title product (140 mg) as an oil.

Workup

  1. customquenched with water
  2. extractionextracted with CH2Cl2
  3. washThe combined organic layers were washed with brine
  4. customdried on Na2SO4
  5. customevaporated to dryness in vacuo
  6. customto afford a residue, which
  7. customwas purified by automated flash liquid chromatography (Horizon™-Biotage)
  8. washeluting with Petroleum Ether-EtOAc 7:3

Sources & evidence

ORD record
ord-a291ef140a3e4f24b9f9f7e03ca7a078
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

Loading…