Sodium Bicarbonate → tert-butyl (4S)-4-(3-fluoropropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

HRID 2401281Notes

Reaction equation

HRID 2401281 reaction equation
O[CH2:2][CH2:3][CH2:4][C@H:5]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].COCCN(S(F)(F)[F:29])CCOC.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[F:29][CH2:2][CH2:3][CH2:4][C@H:5]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 10879805Tert-butyl (4S)-4-(3-hydroxypropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Product 1

HCID 86705185tert-butyl (4S)-4-(3-fluoropropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of tert-butyl (4S)-4-(3-hydroxypropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (3.05 g) in chloroform (40 mL) was cooled in a dry ice-acetone bath, bis(2-methoxyethyl)aminosulfur trifluoride (2.77 mL) was added thereto, and the mixture was stirred at room temperature for 3 hr. Saturated aqueous sodium hydrogen carbonate solution was added thereto, and the organic layer was washed with water and brine, followed by drying with anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=10:1-2:1) to afford tert-butyl (4S)-4-(3-fluoropropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (900 mg).

Workup

  1. washthe organic layer was washed with water and brine
  2. dry with materialby drying with anhydrous sodium sulfate
  3. filtrationAfter the desiccant was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=10:1-2:1)

Sources & evidence

ORD record
ord-64ad1954f1454d219e50008c89813cd9
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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