Diethyl Ether → cis-1,6-Dioxo-4a-(3'-methoxyphenyl)-2-methyldecahydroisoquinoline

HRID 67800ノート

反応式

HRID 67800 の反応式
CC[O:3][CH2:4][CH3:5].[Na+].[Cl-].C(O[CH2:11][C:12]1[C:13](=[O:27])[N:14]([CH3:26])[CH2:15][CH2:16][C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1)=O.[CH2:28]1COCC1>>[O:27]=[C:13]1[C@@H:12]2[C@@:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=3)([CH2:28][C:4](=[O:3])[CH2:5][CH2:11]2)[CH2:16][CH2:15][N:14]1[CH3:26]

参加物

5

反応物 4

HCID 3283Diethyl EtherHCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 129475523-Formyloxymethyl-4-(3'-methoxyphenyl)-1-methyl-5,6-dihydro-2-pyridone

生成物 1

HCID 86736842cis-1,6-Dioxo-4a-(3'-methoxyphenyl)-2-methyldecahydroisoquinoline

実験手順

Ketal cis-34 (Example 16) (20 mg, 0.06 mmol) was dissolved in 1:1 THF/1 N H2SO4 (2 mL) and stirred for 60 h. Ether (2 mL) and saturated NaCl (1 mL) were added, the aqueous phase washed with ether (1 mL), and the combined organic phases washed with saturated NaCl (2 mL), dried, and evaporated to yield 17 mg (99%) of pure cis-9: NMR δ 7.30 (t,J=9 Hz, 1H), 6.9 (m, 3H), 3.78 (s, 3H), 7.87 (s, 3H), 2.63 (s, 2H); IR 1712, 1634, 1603, 1580 cm-1 ; mass spectrum m/e (rel intensity) 287 (32), 218 (26), 55 (100). Anal. Calcd for C17H21NO3 : C, 71.0; H, 7.4; N, 4.9. Found: C, 71.0; H, 7.4; N, 4.9.

後処理

  1. washthe aqueous phase washed with ether (1 mL)
  2. washthe combined organic phases washed with saturated NaCl (2 mL)
  3. customdried
  4. customevaporated
  5. customto yield 17 mg (99%) of pure cis-9

出典と根拠

ORDレコード
ord-e2d5d251e04e40498c31088368b63d64
出典データセット
uspto-grants-1982_08
特許番号
US04346224

反応ノート

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