Pivaloyl chloride → 1,2,3,4,-Tetrahydro-6-trimethylacetoxy-N-3-(2-thienyl)propionylisoquinoline

HRID 1088697Notes

Reaction equation

HRID 1088697 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([C:12](=[O:20])[CH2:13][CH2:14][C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)[CH2:6][CH2:5]2.[CH3:21][C:22]([CH3:27])([CH3:26])[C:23](Cl)=[O:24]>FC(F)(F)C(O)=O>[CH3:21][C:22]([CH3:27])([CH3:26])[C:23]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([C:12](=[O:20])[CH2:13][CH2:14][C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)[CH2:6][CH2:5]2)=[O:24]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 157187121,2,3,4,-Tetrahydro-6-hydroxy-N-3-(2-thienyl)propionylisoquinoline

Product 1

HCID 157187131,2,3,4,-Tetrahydro-6-trimethylacetoxy-N-3-(2-thienyl)propionylisoquinoline

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of the product of Example 14 (2.83 g) in trifluoroacetic acid (30 mL) at 0° C. was added dropwise trimethylacetyl chloride (1.4 mL) and the reaction allowed to warm to room temperature. After 4 hours, the reaction was quenched with water and concentrated, the residue was dissolved in CH2Cl2, washed with brine, dried (MgSO4), filtered and concentrated. Chromatography of the residue on silica gel (elution with 50% ethyl acetate/hexanes) provided 3.8 g of desired product.

Workup

  1. customthe reaction was quenched with water
  2. concentrationconcentrated
  3. dissolutionthe residue was dissolved in CH2Cl2
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ba9e62d145784de8a60c08882c5dbb08
Source dataset
uspto-grants-1990_10
Patent number
US04963563

Reaction notes

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