Tetrahydrofuran → HCID 178445722, compound

HRID 2389137Notes

Reaction equation

HRID 2389137 reaction equation
[Br:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C@:13]1([CH3:19])[CH2:17][O:16][C:15](=[O:18])[NH:14]1)=[CH:7]2.O1CCCC1.[C:25]([C@H:29]1[CH2:34][CH2:33][C@H:32](O)[CH2:31][CH2:30]1)([CH3:28])([CH3:27])[CH3:26].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>>[Br:1][C:2]1[C:11]([O:12][C@H:32]2[CH2:33][CH2:34][C@H:29]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:30][CH2:31]2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C@:13]1([CH3:19])[CH2:17][O:16][C:15](=[O:18])[NH:14]1)=[CH:7]2

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 67413226(R)-4-(5-bromo-6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-oneHCID 178445812HCID 178445812, compound

Product 1

HCID 178445722HCID 178445722, compoundYield 45%

Procedure

(R)-4-(5-Bromo-6-hydroxy-naphthalen-2-yl)-4-methyl-oxazolidin-2-one (2.16 g, 6.70 mmol) was dissolved in tetrahydrofuran (22.50 mL, 277.4 mmol) in a capped 250 mL round-bottom flask equipped with a magnetic stir bar. trans-4-tert-Butyl-cyclohexanol (2.095 g, 13.41 mmol) and triphenylphosphine (3.517 g, 13.41 mmol) were added and the mixture was stirred for 5 minutes. Diisopropyl azodicarboxylate (2.640 mL, 13.41 mmol) was then slowly added and the reaction mixture was stirred at room temperature overnight. The mixture was concentrated in vacuo, diluted in methylene chloride and adsorbed onto silica gel under reduced pressure, then purified by flash chromatography (0-55% EtOAC in hexanes) to give 1.37 g of the title compound (45% yield).

Workup

  1. customequipped with a magnetic stir bar
  2. stirringthe reaction mixture was stirred at room temperature overnight
  3. concentrationThe mixture was concentrated in vacuo
  4. additiondiluted in methylene chloride
  5. custompurified by flash chromatography (0-55% EtOAC in hexanes)

Sources & evidence

ORD record
ord-24798b3d52de4713977be30e35735cd2
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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