Tetrahydrofuran → HCID 178421574, compound

HRID 1036403

Reaction equation

HRID 1036403 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C@:12]1([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]1)[CH:6]=[CH:5]2.O1CCCC1.[CH3:24][C@H:25]1[CH2:30][CH2:29][C@H:28](O)[CH2:27][CH2:26]1.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>>[CH3:18][C@@:12]1([C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([O:1][C@H:28]4[CH2:29][CH2:30][C@@H:25]([CH3:24])[CH2:26][CH2:27]4)[CH:3]=3)[CH:8]=2)[CH2:16][O:15][C:14](=[O:17])[NH:13]1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-oneHCID 178461407HCID 178461407, compound

Product 1

HCID 178421574HCID 178421574, compoundYield 69.8%

Procedure

(R)-4-(6-Hydroxynaphthalen-2-yl)-4-methyl-oxazolidin-2-one (Example 4, 0.3144 g, 0.001292 mol) was dissolved in tetrahydrofuran (5.00 mL, 0.0616 mol) in a capped 40 mL vial. trans-4-Methyl-cyclohexanol (0.177 g, 0.00155 mol) and triphenylphosphine polymer-bound (1.12 g, 0.00207 mol) were added and the mixture was stirred at room temperature. Diisopropyl azodicarboxylate (0.407 mL, 0.00207 mol) was added and the mixture was stirred for 2 days at room temperature. The mixture was filtered through CELITE™, concentrated and purified by flash column chromatography (0-30% EtOAc in methylene chloride) to give 0.3059 g of the title compound (69% yield).

Workup

  1. stirringthe mixture was stirred for 2 days at room temperature
  2. filtrationThe mixture was filtered through CELITE™
  3. concentrationconcentrated
  4. custompurified by flash column chromatography (0-30% EtOAc in methylene chloride)

Sources & evidence

ORD record
ord-9f54c65977f7452c991a6b9e74aa9322
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Linked notes

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