Calcium Carbonate → N-trifluoroacetyl-8-iodo-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 881918ノート

反応式

HRID 881918 の反応式
[F:1][C:2]([F:20])([F:19])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].C([O-])([O-])=O.[Ca+2].[I:26]Cl>CO>[F:20][C:2]([F:1])([F:19])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([I:26])[C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

参加物

5

反応物 3

HCID 10112Calcium CarbonateHCID 24640Iodine chlorideHCID 22292800HCID 22292800、化合物

生成物 1

HCID 22292785N-trifluoroacetyl-8-iodo-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine収率 71.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

A solution of N-trifluoroacetyl-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (1.50 g, 5.22 mmol) in methanol (70 mL) was treated with CaCO3 (1.06 g, 10.44 mmol) followed by a solution of ICl (1.70 g, 10.44 mmol) in methanol (10 mL), and stirred overnight at 20 C. The product mixture was filtered, concentrated, dissolved in EtOAc (200 mL), extracted twice with 5% aqueous sodium bisulfite (100 mL), once with brine (100 mL), dried with Na2SO4 and concentrated. Flash chromatography (15% EtOAc in hexane, silica) resulted in 1.54 g of a white solid. 1H NMR (400 MHz, CDCl3, mixture of rotamers) d 7.55 (m, 1H), 6.57 (m, 1H), 3.86 (s, 3H), 3.80 (m, 1H), 3.60-3.30 (m, 2H), 3.20-2.80 (m, 4H), 1.30 (m, 3H). MS calculated for C14H15F3INO2+H: 414, observed: 414.

後処理

  1. filtrationThe product mixture was filtered
  2. concentrationconcentrated
  3. dissolutiondissolved in EtOAc (200 mL)
  4. extractionextracted twice with 5% aqueous sodium bisulfite (100 mL), once with brine (100 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-769abb7ce53547dc9a904868cfbccbbd
出典データセット
uspto-grants-2015_03
特許番号
US08993750B2

反応ノート

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