Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 57880338, compound

HRID 1360222Notes

Reaction equation

HRID 1360222 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([N:15]2[C@H:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:18][O:17][C:16]2=[O:26])=[O:14])=[CH:5][CH:4]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].C1(S(N2C(C3C=CC=CC=3)O2)(=O)=[O:44])C=CC=CC=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>O1CCCC1.O.C(OCC)(=O)C>[OH:44][C@H:12]([CH2:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:13]([N:15]1[C@H:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:18][O:17][C:16]1=[O:26])=[O:14]

Participants

8

Reactant 4

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 2724254Sodium bis(trimethylsilyl)amideHCID 57880340HCID 57880340, compound

Product 1

HCID 57880338HCID 57880338, compoundYield 71.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

(4R)-3-[5-(4-Methoxyphenyl)pentanoyl]-4-phenyl-1,3-oxazolidin-2-one (Reference Example 20) (1.0 g) was dissolved in tetrahydrofuran (10 ml) and the resulting solution was cooled to −78° C., followed by adding thereto sodium hexamethyldisilazide (1M, 3.4 ml). After 30 minutes, a solution of Davis reagent (0.9 g) in tetrahydrofuran (5 ml) was added dropwise thereto. After stirring for 1 hour, a solution of camphorsulfonic acid (1.5 g) in tetrahydrofuran (5 ml) was added thereto and stirred for 30 minutes. Ethyl acetate and water were added to the reaction mixture to effect separation and extraction. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution, water and a saturated aqueous sodium chloride solution, dried, concentrated, and then the residue was purified by a silica gel chromatography (100 g, ethyl acetate:hexane=1:3) to obtain (4R)-3-[(2R)-2-hydroxy-5-(4-methoxyphenyl)pentanoyl]-4-phenyl-1,3-oxazolidin-2-one (0.75 g).

Workup

  1. additionby adding
  2. stirringstirred for 30 minutes
  3. customseparation and extraction
  4. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution, water
  5. dry with materiala saturated aqueous sodium chloride solution, dried
  6. concentrationconcentrated
  7. customthe residue was purified by a silica gel chromatography (100 g, ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-f768ad7368f04bae8ecff91dee5c0438
Source dataset
uspto-grants-2011_02
Patent number
US07879843B2

Reaction notes

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