Diethyl Ether → cis-2,6-Dimethyl-alpha,alpha-diphenyl-1-piperidinebutanol

HRID 437383ノート

反応式

HRID 437383 の反応式
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCO[CH2:11][CH3:12].[CH3:13][C@H:14]1[CH2:19][CH2:18][CH2:17][C@@H:16]([CH3:20])[N:15]1[CH2:21][CH2:22][CH2:23][C:24]([O:26]C)=O>O>[CH3:20][C@H:16]1[CH2:17][CH2:18][CH2:19][C@@H:14]([CH3:13])[N:15]1[CH2:21][CH2:22][CH2:23][C:24]([C:12]1[CH:11]=[CH:3][CH:2]=[CH:1][CH:6]=1)([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[OH:26]

参加物

5

反応物 3

HCID 3283Diethyl Ether2 回HCID 14810575cis-2,6-Dimethyl-1-piperidinebutyric acid, methyl esterHCID 178506676HCID 178506676、化合物

生成物 1

HCID 14810507cis-2,6-Dimethyl-alpha,alpha-diphenyl-1-piperidinebutanol

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A 2M solution of phenyl lithium in benzene-ether (70 to 30), 100 ml., is added to 100 ml. of dry ether with stirring under a nitrogen atmosphere. The mixture is stirred and cooled to 0°-5° while a solution of 20 g. of cis-2,6-dimethyl-1-piperidinebutyric acid, methyl ester, in 100 ml. of dry ether is added slowly over a period of 15 minutes. After the addition is complete, the mixture is stirred an additional 2.5 hours at 0°-5°, then treated dropwise with 30 ml. of water. The organic layer is separated, washed with water and extracted with an excess of dilute acetic acid. The acid extract is washed with ether, basified with aqueous sodium hydroxide, then extracted with ether. The ether extract is washed with water, dried and evaporated to give cis-2,6-dimethyl-α,α-diphenyl-1-piperidinebutanol; m.p. 90°-91° C. after two crystallizations from petroleum ether.

後処理

  1. addition, is added to 100 ml
  2. temperaturecooled to 0°-5° while a solution of 20 g
  3. additionAfter the addition
  4. stirringthe mixture is stirred an additional 2.5 hours at 0°-5°
  5. additiontreated dropwise with 30 ml
  6. customThe organic layer is separated
  7. washwashed with water
  8. extractionextracted with an excess of dilute acetic acid
  9. extractionThe acid extract
  10. washis washed with ether
  11. extractionextracted with ether
  12. extractionThe ether extract
  13. washis washed with water
  14. customdried
  15. customevaporated

出典と根拠

ORDレコード
ord-37308e8eed334ee18ce3cb2242c0916e
出典データセット
uspto-grants-1977_06
特許番号
US04031101

反応ノート

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