Methanol → HCID 89739114, compound

HRID 2206637Notes

Reaction equation

HRID 2206637 reaction equation
[CH3:1][C:2]([S@:5](/[N:7]=[C:8](/[CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)\[CH3:9])=[O:6])([CH3:4])[CH3:3].CO.[BH4-].[Na+]>O1CCCC1>[CH3:1][C:2]([S@:5]([NH:7][CH:8]([CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[CH3:9])=[O:6])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 88859379HCID 88859379, compound

Product 1

HCID 89739114HCID 89739114, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-32.5 °C

Procedure

To a solution of (R,E)-2-methyl-N-(1-(tetrahydro-2H-pyran-4-yl)ethylidene)propane-2-sulfinamide (1.25 g, 5.4 mmol) in tetrahydrofuran (6 mL) was added methanol (692 mg, 21.6 mmol) and NaBH4 (821 mg, 21.6 mmol) at −65° C. under N2. The reaction was stirred at −65-0° C. for 2 h. Then the reaction was quenched by water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaHCO3 and concentrated in vacuo to give crude (R)-2-methyl-N-(1-(tetrahydro-2H-pyran-4-yl)ethyl)Propane-2-sulfinamide (1.2 g, 52.1%) as a yellow oil.

Workup

  1. customThen the reaction was quenched by water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous NaHCO3
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e29169aa63fb45ca9b46db5e0e984e5a
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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