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

HRID 437383노트

반응식

HRID 437383 반응식
[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]

참가 물질

5

반응물 3

HCID 3283Diethyl Ether2회HCID 14810575cis-2,6-Dimethyl-1-piperidinebutyric acid, methyl esterHCID 178506676HCID 178506676, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-37308e8eed334ee18ce3cb2242c0916e
출처 데이터셋
uspto-grants-1977_06
특허 번호
US04031101

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