Hydrochloric Acid → (3R)-3-[(1R,7aR)-octahydro-4-bromomethylene-7a-methyl-1H-inden-1-yl]butanol

HRID 567407ノート

反応式

HRID 567407 の反応式
[Br:1][CH:2]=[C:3]1[CH2:11][CH2:10][CH2:9][C@@:8]2([CH3:12])[CH:4]1[CH2:5][CH2:6][C@@H:7]2[C@H:13]([CH3:17])[CH2:14][C:15]#N.ClCCl.S([O-])([O-])(=O)=[O:22].[Na+].[Na+].Cl>C(OCC)(=O)C.CO>[Br:1][CH:2]=[C:3]1[CH2:11][CH2:10][CH2:9][C@@:8]2([CH3:12])[CH:4]1[CH2:5][CH2:6][C@@H:7]2[C@H:13]([CH3:17])[CH2:14][CH2:15][OH:22]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 24436Sodium SulfateHCID 70187237(3R)-3-[(1R,7aR)-octahydro-4-bromomethylene-7a-methyl-1H-inden-1-yl]butyronitrile

生成物 1

HCID 70187597(3R)-3-[(1R,7aR)-octahydro-4-bromomethylene-7a-methyl-1H-inden-1-yl]butanol

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-70 °C

実験手順

A 84 mg amount of (3R)-3-[(1R,7aR)-octahydro-4-bromomethylene-7a-methyl-1H-inden-1-yl]butyronitrile was taken in a 25 ml eggplant-shaped flask, then 5 ml of dried dichloromethane was then added to dissolve the same. The solution was cooled by a −70° C. bath, then 660 μl of a 1.5M [(CH3)2CHCH2]2AlH/toluene solution was added dropwise. The solution was stirred at the same temperature for 1 hour, then 0.5 ml of a saturated aqueous solution of sodium sulfate, 0.3 ml of methanol, 0.5 ml of 2N hydrochloric acid, and 15 ml of ethyl acetate were added and the solution stirred for 30 minutes. The reaction solution was filtered by Celite, then was washed by a saturated solution of ammonium chloride and saturated saline, then was dried over anhydrous magnesium sulfate and the desiccant filtered out. The solvent was distilled off under reduced pressure to obtain (3R)-3-[(1R,7aR)-octahydro-4-bromomethylene-7a-methyl-1H-inden-1-yl]butanol in an amount of 85 mg.

後処理

  1. dissolutionto dissolve the same
  2. stirringthe solution stirred for 30 minutes
  3. filtrationThe reaction solution was filtered by Celite
  4. washwas washed by a saturated solution of ammonium chloride and saturated saline
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. filtrationthe desiccant filtered out
  7. distillationThe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-927e6ed3ebc746f0bdbd66b2e6337253
出典データセット
uspto-grants-2001_01
特許番号
US06177586B1

反応ノート

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