Hydrochloric Acid → trans-Octahydroquinolin-2-one

HRID 352176ノート

反応式

HRID 352176 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 12265804trans-Octahydroquinolin-2-one

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-37acb5cdc9294d4b88aa3eead5bf4be9
出典データセット
uspto-grants-2004_06
特許番号
US06743794B2

反応ノート

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