Hydrochloric Acid → HCID 89713532, compound

HRID 881996Notes

Reaction equation

HRID 881996 reaction equation
[CH3:1][CH:2]([CH3:17])[CH2:3][CH:4]([CH2:9][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[C:5]([O:7]C)=O.Cl.[CH:19]([Mg]Cl)(C)C.[NH4+:24].[Cl-].C1C[O:29][CH2:28]C1>>[CH3:28][O:29][N:24]([CH3:19])[C:5](=[O:7])[CH:4]([CH2:9][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH2:3][CH:2]([CH3:1])[CH3:17]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 89713455HCID 89713455, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 89713532HCID 89713532, compoundYield 93%

Conditions

Temperature
-20 °C

Procedure

Methyl 4-methyl-2-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)pentanoate (251 mg, 1.08 mmol) and Me(MeO)NH.HCl (157 mg, 1.61 mmol) were added to anhydrous THF (3 mL) and the mixture was cooled to −20° C. under nitrogen charge. An i-PrMgCl solution (1.62 mL, 2.0 M) dissolved in THF was slowly added thereto over 15 min by using a syringe. The mixture was further stirred at −10° C. for 20 min, and then a saturated NH4Cl aqueous solution (2 mL) was added thereto to complete the reaction. Extraction was performed by using ethyl acetate, anhydrous magnesium sulfate was used to perform drying and distillation under reduced pressure, and then column chromatography was used to obtain 270 mg (yield 93%) of the title compound.

Workup

  1. additioncharge
  2. additionwas slowly added
  3. customthe reaction
  4. extractionExtraction
  5. customto perform drying
  6. distillationdistillation under reduced pressure

Sources & evidence

ORD record
ord-405277f7428a41b8a10751dfc90d5e24
Source dataset
uspto-grants-2015_03
Patent number
US08993766B2

Reaction notes

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