Lithium Hexamethyldisilazide → 4(R)-benzyl-3-{2-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-3-methylbutyryl}oxazolidin-2-one

HRID 252415Notes

Reaction equation

HRID 252415 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:19])[CH2:15][CH:16]([CH3:18])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:31][C:32]1[CH:41]=[C:40]2[C:35]([CH:36]=[CH:37][CH:38]=[C:39]2[O:42][CH2:43][CH2:44][O:45][CH3:46])=[CH:34][CH:33]=1>O1CCCC1>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:19])[CH:15]([CH2:31][C:32]1[CH:33]=[CH:34][C:35]2[C:40](=[C:39]([O:42][CH2:43][CH2:44][O:45][CH3:46])[CH:38]=[CH:37][CH:36]=2)[CH:41]=1)[CH:16]([CH3:17])[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 11391340(4R)-4-Benzyl-3-(3-methylbutanoyl)-1,3-oxazolidin-2-oneHCID 668888517-Bromomethyl-1-(2-methoxyethoxy)naphthalene

Product 1

HCID 668877734(R)-benzyl-3-{2-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-3-methylbutyryl}oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.31 g of 4(R)-benzyl-3-(3-methylbutyryl)oxazolidin-2-one in 2 ml of tetrahydrofuran is added dropwise at −78° C. to 1.2 ml of lithium bis(trimethylsilyl)amide solution (1M in tetrahydrofuran). After 30 minutes, a solution of 0.30 g of 7-bromomethyl-1-(2-methoxyethoxy)naphthalene in 2 ml of tetrahydrofuran is added dropwise and the reaction mixture is allowed to thaw from −78° C. to 0° C. over 2 hours. After 3 hours at 0° C., the reaction mixture is quenched with 5 ml of 1M ammonium chloride solution, diluted with water and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed with brine, dried over sodium sulphate and concentrated by evaporation. The title compound is identified on the basis of the Rf value from the residue by means of flash chromatography (SiO2 60F).

Workup

  1. customthaw from −78° C. to 0° C.
  2. customover 2 hours
  3. waitAfter 3 hours at 0° C.
  4. customthe reaction mixture is quenched with 5 ml of 1M ammonium chloride solution
  5. additiondiluted with water
  6. extractionextracted with tert-butyl methyl ether (2×)
  7. washThe combined organic phases are washed with brine
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-615f61919243407cb637b7651cdede4f
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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