Acetic Anhydride → (R)(+)-N-(1,2,3,4-Tetrahydro-1-naphthyl)-N-methylformamide

HRID 1756876

反応式

HRID 1756876 の反応式
C(O[C:5](=[O:7])C)(=O)C.C(OC(=O)C)=O.[CH3:14][NH:15][C@H:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][CH2:17]1.[OH-].[Na+]>C(O)=O>[C@H:16]1([N:15]([CH3:14])[CH:5]=[O:7])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][CH2:17]1

参加物

6

反応物 4

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 75269Acetic-formic anhydrideHCID 7128544(R)-N-Methyl-1,2,3,4-tetrahydronaphthalen-1-amine

生成物 1

HCID 22855465(R)(+)-N-(1,2,3,4-Tetrahydro-1-naphthyl)-N-methylformamide収率 96.6%

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒2 回

反応条件

温度
50 °C

実験手順

Acetic anhydride (54.1 g) was chilled to 0° C. and stirred as 98% formic acid (33.1 g) was added over 30 minutes, keeping the temperature below 5° C. The solution was warmed to 50° C., held at this temperature for 15 minutes, and chilled to 5° C. The resulting solution of acetic-formic anhydride was added over 5 minutes to a stirred, chilled solution of (R)(-)-N-methyl-1,2,3,4-tetrahydro-1-naphthylamine (19.08 g) in 98% formic acid (19.08 ml), keeping the temperature below 10° C. The reaction solution was warmed to room temperature, stirred for 1 hour, poured into an ice-water mixture (200 g) and stirred for 30 minutes. The mixture was basified to pH 9 with 10N aqueous sodium hydroxide solution (about 230 ml) and extracted with dichloromethane (3×200 ml). The combined extracts were back-washed with 1N aqueous hydrochloric acid (100 ml), then water (100 ml), and evaporated under vacuum to give the title compound (21.63 g, 96.6%) as a solid, m.p. 53°-55° C.; Rf 0.80 (silica; chloroform, methanol; 95:5).

後処理

  1. additionwas added over 30 minutes
  2. customthe temperature below 5° C
  3. temperaturechilled to 5° C
  4. customthe temperature below 10° C
  5. temperatureThe reaction solution was warmed to room temperature
  6. stirringstirred for 30 minutes
  7. extractionextracted with dichloromethane (3×200 ml)
  8. washThe combined extracts were back-washed with 1N aqueous hydrochloric acid (100 ml)
  9. customwater (100 ml), and evaporated under vacuum

出典と根拠

ORDレコード
ord-1a6cdb205f65431590eb2889b464069b
出典データセット
uspto-grants-1995_08
特許番号
US05442116

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