Triphenylphosphine → (R)-4-methyl-4-(6-(4-(trifluoromethyl)cyclohexyloxy)naphthalen-2-yl)oxazolidin-2-one

HRID 1036514Notes

Reaction equation

HRID 1036514 reaction equation
[F:1][C:2]([F:11])([F:10])[CH:3]1[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1.O[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([C@:23]1([CH3:29])[CH2:27][O:26][C:25](=[O:28])[NH:24]1)[CH:17]=[CH:16]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH3:29][C@@:23]1([C:18]2[CH:17]=[CH:16][C:15]3[C:20](=[CH:21][CH:22]=[C:13]([O:9][CH:6]4[CH2:5][CH2:4][CH:3]([C:2]([F:10])([F:11])[F:1])[CH2:8][CH2:7]4)[CH:14]=3)[CH:19]=2)[CH2:27][O:26][C:25](=[O:28])[NH:24]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 27797654-(Trifluoromethyl)cyclohexan-1-olHCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

Product 1

HCID 67412717(R)-4-methyl-4-(6-(4-(trifluoromethyl)cyclohexyloxy)naphthalen-2-yl)oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 40 mL vial, 4-trifluoromethyl-cyclohexanol (713.2 mg, 0.004241 mol) was diluted with tetrahydrofuran (19.0 mL), then (R)-4-(6-hydroxy-naphthalen-2-yl)-4-methyl-oxazolidin-2-one (0.9462 g, 0.003890 mol) and triphenylphosphine (1.3031 g, 0.0049682 mol) were added. The mixture was stirred and then diisopropyl azodicarboxylate (0.91 mL, 0.0046 mol) was added. The reaction was stirred at room temperature for 38 h. The reaction mixture was concentrated in vacuo, taken up in DCM, adsorbed onto silica gel and chromatographed (0-100% EtOAc/Hexanes). Isolated was 223.5 mg (15%) of product as cis/trans mixture.

Workup

  1. stirringThe reaction was stirred at room temperature for 38 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customchromatographed (0-100% EtOAc/Hexanes)
  4. customIsolated

Sources & evidence

ORD record
ord-634278de22c040ddb4a64c9a3d4a7490
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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