Diisopropylethylamine → 2-Naphthol

HRID 892812Notes

Reaction equation

HRID 892812 reaction equation
C1(C)C=CC(S(OCC[C@:13]2([OH:27])[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18](F)[CH:19]=3)[C@H:14]2C(C)C)(=O)=O)=CC=1.C(N(C(C)C)C(C)C)C>CS(C)=O>[CH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[OH:27]

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 54277958HCID 54277958, compound

Product 1

HCID 86632-Naphthol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 12.6 g (0.031 mol) of [1R,2R]-(-)-2-[6-fluoro-1,2,3,4-tetrahydro-2-hydroxy-1-isopropyl-2-naphthyl]ethyl p-toluenesulphonate, 6.1 g (0.031 mol) of 3,4-(methylenedioxy)-N-methyl-β-phenethylamine and 5.3 ml (0.031 mol) of ethyldiisopropylamine in 50 ml of dimethyl sulfoxide was stirred under a nitrogen atmosphere for 3 hours at 80° and thereafter concentrated in a high vacuum. The residue was dissolved in methylene chloride and the solution obtained was washed with a saturated sodium carbonate solution and extracted three times with 3N hydrochloric acid. The aqueous extracts were made alkaline with a 28% sodium hydroxide solution. The oily suspension was extracted three times with methylene chloride. The organic extracts were dried and evaporated under reduced pressure. The residual oil was chromatographed on silica gel with ethyl acetate/methanol (9:1), yielding 9.3 g (73%) of [1R,2R]-(-)-6-fluoro-1,2,3,4-tetrahydro-1-isopropyl-2-[[3,4-(methylenedioxy)phenethyl]methylamino]ethyl]-2-naphthalenol as a yellowish oil; [α]D20 =-22.1°.

Workup

  1. concentrationconcentrated in a high vacuum
  2. dissolutionThe residue was dissolved in methylene chloride
  3. customthe solution obtained
  4. washwas washed with a saturated sodium carbonate solution
  5. extractionextracted three times with 3N hydrochloric acid
  6. extractionThe oily suspension was extracted three times with methylene chloride
  7. customThe organic extracts were dried
  8. customevaporated under reduced pressure
  9. customThe residual oil was chromatographed on silica gel with ethyl acetate/methanol (9:1)

Sources & evidence

ORD record
ord-5d8d463979fc41048233e9bced2468ce
Source dataset
uspto-grants-1992_06
Patent number
US05120759

Reaction notes

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