Naphthalene → HCID 59218163, compound

HRID 2246943Notes

Reaction equation

HRID 2246943 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:14][C@H:13]([CH2:15][C@H:16]([S:18][CH3:19])[CH3:17])[NH:12][CH2:11][C@@H:10]2[O:20][CH:21]([C:32]2[CH:33]=[CH:34][C:35]3[O:40][CH2:39][CH2:38][N:37]([CH2:41][CH2:42][CH2:43][O:44][CH3:45])[C:36]=3[CH:46]=2)S(C2C=CC(C)=CC=2)(=O)=O)=[CH:5][CH:4]=1.C1C2C(=CC=CC=2)C=CC=1.[Na]>C(COC)OC.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:14][C@H:13]([CH2:15][C@H:16]([S:18][CH3:19])[CH3:17])[NH:12][CH2:11][C@@H:10]2[O:20][CH2:21][C:32]2[CH:33]=[CH:34][C:35]3[O:40][CH2:39][CH2:38][N:37]([CH2:41][CH2:42][CH2:43][O:44][CH3:45])[C:36]=3[CH:46]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 931NaphthaleneHCID 5360545SodiumHCID 68443450HCID 68443450, compound

Product 1

HCID 59218163HCID 59218163, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 92 mg of 6-[(3R,4R,6R)-4-(4-methoxy-phenyl)-6-((R)-2-methylsulfanyl-propyl)-1-(toluene-4-sulfonyl)-piperidin-3-yloxymethyl]-4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazine (diastereomer 1) in 2.0 ml of dimethoxyethane are added 100 mg of naphthalene and 20 mg of sodium. The reaction mixture is sonicated for 10 minutes, diluted with water and extracted with dichloromethane. The organic phases are combined, dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by flash chromatography (SiO2 60 F) to afford the title compound.

Workup

  1. customThe reaction mixture is sonicated for 10 minutes
  2. extractionextracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-42f1447974df42fea8d2bd6aa8a1345f
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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