Ammonium Chloride → HCID 60004308, compound

HRID 2401274Notes

Reaction equation

HRID 2401274 reaction equation
[CH:1]([C@H:3]1[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[N:4]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:2].[CH2:17]([Mg]Br)[CH3:18].[Cl-].[NH4+]>C1COCC1>[OH:2][CH:1]([C@H:3]1[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[N:4]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 1787923-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)-HCID 178418443HCID 178418443, compound

Product 1

HCID 60004308HCID 60004308, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl (4R)-4-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (14.0 g) in THF (250 mL) was cooled in a dry ice/acetone bath under nitrogen atmosphere, and ethyl magnesium bromide (24 mL, 3M solution in diethyl ether) was added dropwise thereto. The resulting mixture was stirred for 3 hr while elevating the temperature gradually to 0° C., and saturated aqueous ammonium chloride solution was added thereto. The mixture was separated into phases, the aqueous layer was then extracted with ethyl acetate, and the organic layer was washed with water and brine. After drying over anhydrous magnesium sulfate, the desiccant was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=92:8-37:63) to afford tert-butyl (4R)-4-(1-hydroxypropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (11.14 g).

Workup

  1. customgradually to 0° C.
  2. customThe mixture was separated into phases
  3. extractionthe aqueous layer was then extracted with ethyl acetate
  4. washthe organic layer was washed with water and brine
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. filtrationthe desiccant was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=92:8-37:63)

Sources & evidence

ORD record
ord-e04a83e2d8f24e6b8b146873861ee6b2
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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