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

HRID 1577980ノート

反応式

HRID 1577980 の反応式
C1CO[C:3]2([CH2:12][CH2:11][C@H:10]3[C@:5]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=4)([CH2:6][CH2:7][N:8]([CH3:14])[C:9]3=[O:13])[CH2:4]2)[O:2]1.CCOCC.[Na+].[Cl-].C(OCC1C(=O)N(C)CCC=1C1C=CC=C(OC)C=1)=O>C1COCC1>[O:13]=[C:9]1[C@@H:10]2[C@@:5]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=3)([CH2:4][C:3](=[O:2])[CH2:12][CH2:11]2)[CH2:6][CH2:7][N:8]1[CH3:14]

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 5234Sodium ChlorideHCID 129475523-Formyloxymethyl-4-(3'-methoxyphenyl)-1-methyl-5,6-dihydro-2-pyridoneHCID 86736843HCID 86736843、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

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-16b243041a5d4c3798f26df96b38954f
出典データセット
uspto-grants-1981_09
特許番号
US04289882

反応ノート

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