(Diethylamino)sulfur trifluoride → HCID 118062725, compound

HRID 920772Notes

Reaction equation

HRID 920772 reaction equation
O[C:2]1([CH3:11])[CH2:5][CH:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3]1.CCN(S(F)(F)[F:18])CC>C(Cl)Cl>[F:18][C:2]1([CH3:11])[CH2:5][CH:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 118061622HCID 118061622, compound

Product 1

HCID 118062725HCID 118062725, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 3-hydroxy-3-methylcyclobutanecarboxylate (500 mg, 3.16 mmol) in DCM (5 mL) was added DAST (0.626 mL, 4.74 mmol) at −78° C. and the reaction mixture was slowly allowed to warm to RT and stir for 3 h. The reaction mixture was diluted with DCM (25 mL), washed with H2O and a saturated aq. solution of NaHCO3, then dried over Na2SO4, filtered and concentrated. The crude product was purified by silica gel chromatography (12 g REDISEP® column, eluting with 25% EtOAc in hexanes). Fractions containing the product were combined and evaporated to afford Intermediate 288A as a pale yellow liquid (0.2 g, 40% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.08 (q, J=7.0 Hz, 2H), 3.22-3.09 (m, 1H), 2.60-2.53 (m, 1H), 2.37-2.22 (m, 3H), 1.44 (d, J=18 Hz, 3H), 1.22-1.11 (m, 3H).

Workup

  1. washwashed with H2O
  2. dry with materiala saturated aq. solution of NaHCO3, then dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel chromatography (12 g REDISEP® column, eluting with 25% EtOAc in hexanes)
  6. additionFractions containing the product
  7. customevaporated

Sources & evidence

ORD record
ord-ff098f4ec5de457b8c49130e7a3ad5be
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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