3,4-dihydro-2H-pyran → 5-(Tetrahydropyran-2-yloxy)-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin

HRID 1416356Notes

Reaction equation

HRID 1416356 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:7]2.[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[O:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:12](=[O:17])[C:13]([F:16])([F:14])[F:15])[CH2:7]2

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 154910662-Trifluoroacetyl-1,2,3,4-tetrahydro-5-isoquinolinol

Product 1

HCID 154342975-(Tetrahydropyran-2-yloxy)-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.7 g (15.9 mmol) of 5-hydroxy-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline (Example 1) and 4.4 mL (47.7 mmol) 2,3-dihydropyrane were dissolved in dichloromethane and catalytic amount of p-toluenesulfonic acid monohydrate was added. After completion of the reaction (System A), the reaction mixture was diluted with dichloromethane, washed with water and aqueous sodium chloride. The solution was dried over Na2SO4, evaporated to dryness, and the product was purified by silicagel chromatography (System A). Yield 4.13 g, 79%. 1H NMR (CDCl3, 400 MHz): 7.16 (1H, m), 7.00 (1H, m), 6.77 (1H, m), 5.45 (1H, m), 4.79 (2H, ss), 3.8 (3H, m), 3.6 (1H, m), 2.9 (4H, m).

Workup

  1. customAfter completion of the reaction (System A), the reaction mixture
  2. washwashed with water and aqueous sodium chloride
  3. dry with materialThe solution was dried over Na2SO4
  4. customevaporated to dryness
  5. customthe product was purified by silicagel chromatography (System A)

Sources & evidence

ORD record
ord-b889aade26804b538c19425e381f7305
Source dataset
uspto-grants-1999_06
Patent number
US05912342

Reaction notes

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