Tetrahydrofuran → HCID 178455814, compound

HRID 2389065Notes

Reaction equation

HRID 2389065 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.[CH2:19]([C@H:21]1[CH2:26][CH2:25][C@H:24](O)[CH2:23][CH2:22]1)[CH3:20].O1CCCC1.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>C(OCC)(=O)C>[CH2:19]([C@@H:21]1[CH2:26][CH2:25][C@H:24]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[C:7]([C@:12]2([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]2)[CH:6]=[CH:5]3)[CH2:23][CH2:22]1)[CH3:20]

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-oneHCID 178455817HCID 178455817, compound

Product 1

HCID 178455814HCID 178455814, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(R)-4-(6-Hydroxynaphthalen-2-yl)-4-methyl-oxazolidin-2-one (0.3594 g, 0.001477 mol) was added to a capped 40 mL vial. trans-4-Ethylcyclohexanol (0.227 g, 0.00177 mol) was added, followed by tetrahydrofuran (6.00 mL, 0.0740 mol). Triphenylphosphine polymer-bound (1.28 g, 0.00236 mol) was added and the mixture was stirred for 5 minutes. Diisopropyl azodicarboxylate (0.465 mL, 0.00236 mol) was added and the mixture was stirred for 48 hours at room temperature. The mixture was diluted in ethyl acetate, filtered through CELITE™, concentrated under vacuum and purified by flash chromatography (0-20% EtOAc in methylene chloride) to give 0.4603 g of the title compound (88% yield).

Workup

  1. stirringthe mixture was stirred for 48 hours at room temperature
  2. filtrationfiltered through CELITE™
  3. concentrationconcentrated under vacuum
  4. custompurified by flash chromatography (0-20% EtOAc in methylene chloride)

Sources & evidence

ORD record
ord-ef979ddda6df4495be897bdf7d7efdec
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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