Pivaloyl chloride → HCID 18604484, compound

HRID 64999Notes

Reaction equation

HRID 64999 reaction equation
[BrH:1].[OH:2][C:3]1[C:16]2[CH2:15][CH2:14][C@H:13]3[C@@H:8]([CH2:9][CH2:10][CH2:11][NH:12]3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]>FC(F)(F)C(O)=O>[BrH:1].[C:17]([O:2][C:3]1[C:16]2[CH2:15][CH2:14][C@H:13]3[C@@H:8]([CH2:9][CH2:10][CH2:11][NH:12]3)[C:7]=2[CH:6]=[CH:5][CH:4]=1)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 9882256(+/-)-trans-7-Hydroxy-1,2,3,4,4a,5,6,10b-octahydrobenzo(f)quinoline hydrobromide

Product 1

HCID 18604484HCID 18604484, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(±)-trans-7-Hydroxy-1,2,3,4,4a,5,6,10b-octahydrobenzo(f)quinoline hydrobromide (50 mg, 0.17 mmol) was dissolved in trifluoroacetic acid (1 ml). Pivaloyl chloride (0.2 ml) was added and the mixture was stirred at room temperature overnight. After evaporation of the solvent, the residue was partitioned between H2O and CH2Cl2. The organic layer was concentrated and applied to a SiO2 column and the product was eluted with CH2Cl2 -MeOH. Fractions containing the product were collected. The solvent was evaporated yielding 20 mg of an oil. GC-MS: M+ at m/e 287.

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was partitioned between H2O and CH2Cl2
  3. concentrationThe organic layer was concentrated
  4. washthe product was eluted with CH2Cl2 -MeOH
  5. additionFractions containing the product
  6. customwere collected
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-fdba1475d808437296ab4bd09fdf9cde
Source dataset
uspto-grants-1986_09
Patent number
US04612316

Reaction notes

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