Hydrochloric Acid → trans-Octahydroquinolin-2-one

HRID 352176Notes

Reaction equation

HRID 352176 reaction equation
[NH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH2:4][CH2:3][C:2]1=[O:11].[BH3-]C#N.[Na+].Cl>O1CCOCC1.CCOC(C)=O>[NH:1]1[C@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][C:2]1=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7360043,4,5,6,7,8-Hexahydro-2(1H)-quinolinoneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 12265804trans-Octahydroquinolin-2-one

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3,4,5,6,7,8-hexahydro-1H-quinoline-2-one (0.1 g, 0.66 mmol) in dioxane (10 mL) containing a catalytic quantity (40 μL) was added NaCNBH3 (0.67 g). The reduction was left to stir for 20 hrs at r.t., and then diluted with EtOAc. The organic phase was treated with dilute HCl (3×), and the combined organics were washed with saturated HCO3−, brine, dried over Na2SO4, filtered and concentrated to afford the mainly traits product (98 mg, 95%, 15-20% cis isomer). MS (+ES) m/z 254 (M+1)+.

Workup

  1. waitThe reduction was left
  2. washthe combined organics were washed with saturated HCO3−, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford the mainly traits product (98 mg, 95%, 15-20% cis isomer)

Sources & evidence

ORD record
ord-37acb5cdc9294d4b88aa3eead5bf4be9
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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