Hydrochloric Acid → trans-Octahydroquinolin-2-one

HRID 352176노트

반응식

HRID 352176 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 12265804trans-Octahydroquinolin-2-one

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-37acb5cdc9294d4b88aa3eead5bf4be9
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743794B2

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