2,2-Dimethoxypropane → Tert-butyl (4S)-4-(3-hydroxypropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

HRID 2401280Notes

Reaction equation

HRID 2401280 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@@H:8]([CH2:11][CH2:12][CH2:13][OH:14])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].CO[C:18](OC)([CH3:20])[CH3:19].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[OH:14][CH2:13][CH2:12][CH2:11][C@H:8]1[CH2:9][O:10][C:18]([CH3:20])([CH3:19])[N:7]1[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:15]

Participants

6

Reactant 4

HCID 64952,2-DimethoxypropaneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 2734851tert-Butyl hydrogen (1,5-dihydroxypentan-2-yl)carbonimidate

Product 1

HCID 10879805Tert-butyl (4S)-4-(3-hydroxypropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of tert-butyl[(2S)-1,5-dihydroxypentan-2-yl]carbamate (9.45 g), 2,2-dimethoxypropane (48 mL) and p-toluenesulfonic acid monohydrate (0.41 g) in chloroform (100 mL) was stirred at room temperature for 3 hr. Saturated aqueous sodium hydrogen carbonate solution was added thereto, and the solvent was distilled off under reduced pressure. Ethyl acetate was added thereto, and the resulting mixture was washed with water and brine, followed by drying over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure and purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=10:1-0:100) to afford tert-butyl (4S)-4-(3-hydroxypropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (3.05 g).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionEthyl acetate was added
  3. washthe resulting mixture was washed with water and brine
  4. dry with materialby drying over anhydrous sodium sulfate
  5. filtrationAfter the desiccant was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. custompurified by column chromatography (silica gel cartridge, hexane/ethyl acetate=10:1-0:100)

Sources & evidence

ORD record
ord-8d217c071a8f4e69a9ecd38399467e77
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

Loading…