Water → HCID 54508834、化合物

HRID 1885744ノート

反応式

HRID 1885744 の反応式
[Cl:1][C:2]1[CH2:3][N:4]=[CH:5][C:6]2([CH3:19])[CH:17]([CH3:18])[CH:15]3[CH2:16][C:10]4=[C:11]([NH:14]3)[CH2:12][CH2:13][C:7]2=[C:8]4[CH:9]=1.[CH:20](N(C(C)C)CC)([CH3:22])[CH3:21].C(Br)C=C.O>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH2:3][N:4]=[CH:5][C:6]2([CH3:19])[CH:17]([CH3:18])[CH:15]3[CH2:16][C:10]4=[C:11]([N:14]3[CH2:22][CH:20]=[CH2:21])[CH2:12][CH2:13][C:7]2=[C:8]4[CH:9]=1

参加物

7

反応物 4

HCID 962WaterHCID 7841Allyl bromideHCID 81531DiisopropylethylamineHCID 73656239HCID 73656239、化合物

生成物 1

HCID 54508834HCID 54508834、化合物収率 47%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 1.30 g of 10-chloro-6,12-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-9H-pyrrolo[3,2-h][3]benzazocine, and 24 ml of dimethylformamide was added 1.69 ml of diisopropylethyl amine. Upon cooling to 0° C., the mixture was cooled to 0° C. and 0.45 ml of allyl bromide in 5.0 ml of dimethylformamide was added, under nitrogen. The mixture was stirred an additional 3 hr at 0° C. and was poured into water and ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate and ether. The combined organic layers were washed with brine, dried over anhydrous potassium carbonate, filtered, and concentrated. The residue crystallized on standing. Recrystallization from ether with ether-pentane and pentane washing gave 0.75 g (47%) of product, mp 189°-191° C.

後処理

  1. temperaturethe mixture was cooled to 0° C.
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate and ether
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous potassium carbonate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue crystallized
  9. customRecrystallization from ether with ether-pentane and pentane washing

出典と根拠

ORDレコード
ord-e329edcc99d64fce8c4eba5a7b41cf50
出典データセット
uspto-grants-1992_09
特許番号
US05145965

反応ノート

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