Water → HCID 59273085, compound

HRID 906979Notes

Reaction equation

HRID 906979 reaction equation
[OH:1][C@H:2]1[CH2:6][C@@H:5]([CH2:7][Si](C)(C)C)[N:4]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[C@H:3]1[CH3:22].CC(C)([O-])C.[K+].C1OCCOCCOCCOCCOCCOC1.O>CS(C)=O>[OH:1][C@H:2]1[CH2:6][C@@H:5]([CH3:7])[N:4]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[C@H:3]1[CH3:22]

Participants

6

Reactant 4

HCID 962Water2×HCID 2855718-Crown-6HCID 10471336HCID 10471336, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 59273085HCID 59273085, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution (12 mL) of benzyl (2S,3S,5S)-3-hydroxy-2-methyl-5-[(trimethylsilyl)methyl]pyrrolidine-1-carboxylate (222 mg) synthesized according to the method described in Journal of Organic Chemistry, vol. 59, pages 1958-1960 (1994), potassium tert-butoxide (130 mg) and 18-crown-6-ether (53 mg) in DMSO was added water (0.6 mL), and the mixture was stirred at 100° C. for 17 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→2/3) to give the title compound as colorless oil (yield: 112 mg, yield: 65%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→2/3)

Sources & evidence

ORD record
ord-bc564e2b7e2a48ee94493543acf721a4
Source dataset
uspto-grants-2011_09
Patent number
US08013008B2

Reaction notes

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