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

HRID 67800노트

반응식

HRID 67800 반응식
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]

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e2d5d251e04e40498c31088368b63d64
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04346224

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