Tetrahydrofuran → (R)-4-{6-[4-(1,1-dimethylpropyl)-cyclohexyloxy]-naphthalen-2-yl}-4-methyloxazolidin-2-one

HRID 2389056Notes

Reaction equation

HRID 2389056 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.[CH3:19][C:20]([CH:24]1[CH2:29][CH2:28][CH:27](O)[CH2:26][CH2:25]1)([CH3:23])[CH2:21][CH3:22].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>>[CH3:23][C:20]([CH:24]1[CH2:25][CH2:26][CH:27]([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)[CH2:28][CH2:29]1)([CH3:19])[CH2:21][CH3:22]

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 79302Cyclohexanol, 4-(1,1-dimethylpropyl)-HCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

Product 1

HCID 67411594(R)-4-{6-[4-(1,1-dimethylpropyl)-cyclohexyloxy]-naphthalen-2-yl}-4-methyloxazolidin-2-oneYield 84%

Procedure

To a mixture of (R)-4-(6-hydroxy-naphthalen-2-yl)-4-methyl-oxazolidin-2-one (Example 4, 300.0 mg, 1.233 mmol) and 4-(1,1-dimethyl-propyl)-cyclohexanol (252 mg, 1.48 mmol) in tetrahydrofuran (5 mL, 60 mmol) was added triphenylphosphine polymer-bound (1.07 g, 1.97 mmol). After the mixture was stirred at room temperate for 10 min, diisopropyl azodicarboxylate (0.388 mL, 1.97 mmol) was added dropwise. The mixture was stirred at room temperate for 48 hrs. The insoluble material was passed over a CELITE™ bed and washed with ethyl acetate. After the solvent was concentrated, the residue was purified with silica gel column eluted with ethyl acetate in hexanes from 0 to 40% to give 410 mg of white precipitate (R)-4-{6-[4-(1,1-dimethylpropyl)-cyclohexyloxy]-naphthalen-2-yl}-4-methyloxazolidin-2-one (84% yield). MS: m/z=396.30 M+H.

Workup

  1. stirringThe mixture was stirred at room temperate for 48 hrs
  2. washwashed with ethyl acetate
  3. concentrationAfter the solvent was concentrated
  4. customthe residue was purified with silica gel column
  5. washeluted with ethyl acetate in hexanes from 0 to 40%

Sources & evidence

ORD record
ord-6b10d737d01943b8b43b61e5b6b93e98
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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