(Bis(2-methoxyethyl)amino)sulfur trifluoride → HCID 89686732, compound

HRID 520430Notes

Reaction equation

HRID 520430 reaction equation
COCCN(S(F)(F)[F:11])CCOC.O[CH2:15][C:16]1([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1>>[F:11][CH2:15][C:16]1([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1

Participants

3

Reactant 2

HCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 86690128HCID 86690128, compound

Product 1

HCID 89686732HCID 89686732, compoundYield 63%

Conditions

Temperature
70 °C

Procedure

Neat Deoxo-Fluor® (342 mg, 1.546 mmol) was added to a cold (0° C.) stirred ethyl 2-(hydroxymethyl)tetrahydro-2H-pyran-2-carboxylate (194 mg, 1.031 mmol) and the mixture was heated at 70° C. overnight. The reaction was quenched with ice and neutralized with sat. aq. NaHCO3 and extracted with DCM (2×). The combined organic layers were washed with water, brine and dried (MgSO4), filtered and dried to give a yellow-orange oil which was purified by silica gel FCC (0-5% EtOAc in DCM) to afford ethyl 2-(fluoromethyl)tetrahydro-2H-pyran-2-carboxylate as a colorless oil (125 mg, 63%) which was saponified (LiOH.H2O, MeOH-THF—H2O, sonicate) to afford Cap P-43 as a viscous oil (82 mg, 77%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.66-4.54 (m, 1H), 4.54-4.41 (m, 1H), 4.02-3.84 (m, 2H), 1.98-1.84 (m, 1H), 1.84-1.72 (m, 2H), 1.69-1.52 (m, 4H).

Workup

  1. customThe reaction was quenched with ice and neutralized with sat. aq. NaHCO3
  2. extractionextracted with DCM (2×)
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customdried
  7. customto give a yellow-orange oil which
  8. customwas purified by silica gel FCC (0-5% EtOAc in DCM)

Sources & evidence

ORD record
ord-912978ccb3c74fa9a04f311ea8cbdfb0
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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