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Chlorotrimethylsilane → (2R,3R)-1-(Dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol HCl

HRID 2394978
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HRID 2394978 반응식
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.[CH3:11][N:12]([CH3:20])[CH2:13][CH:14]([CH3:19])[C:15](=[O:18])[CH2:16][CH3:17].[Cl-].[NH4+].C[Si](C)(C)[Cl:25]>O1CCCC1.CCOCC.CC(=O)CC.O>[ClH:25].[CH3:11][N:12]([CH3:20])[CH2:13][CH:14]([CH3:19])[C:15]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1)([OH:18])[CH2:16][CH3:17]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 5

HCID 6397ChlorotrimethylsilaneHCID 169713-BromoanisoleHCID 25517Ammonium ChlorideHCID 30487291-(Dimethylamino)-2-methyl-3-pentanoneHCID 5462224Magnesium

생성물 1

HCID 18974517(2R,3R)-1-(Dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol HCl수율 47.4%

시약·촉매·용매

4
HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6569Methyl Ethyl Ketone용매HCID 8028Tetrahydrofuran용매3회

실험 절차

27.0 g (1.11 mole) of magnesium turnings were stirred in 150 ml tetrahydrofuran and 207.6 g (1.11 mole) 1-bromo-3-methoxy-benzene, dissolved in 400 ml tetrahydrofuran, were added drop-wise. The mixture was heated for one hour under reflux and was subsequently cooled to a temperature between 5° C. and 10° C. 128.30 g (0.89 mole) (RS)-1-dimethylamino-2-methyl-pentan-3-one, dissolved in 400 ml tetrahydrofuran, were added drop-wise at this temperature. The reaction mixture was allowed to stand and was subsequently cooled again to a temperature between 5° C. and 10° C. After adding 300 ml of 20 weight % ammonium chloride solution, the mixture was diluted with 400 ml ether. After phase separation the batch was extracted twice with ether, dried over sodium sulphate and the solvent was removed by distillation. The residue obtained was taken up in 3.2 l 2-butanone and treated with 120.60 g (1.11 mole) trimethylchlorosilane and 20 ml water. 121.5 g of hydrochloride (2) (38% theoretical) with a melting point of 198°-199° C. were obtained. 2nd step:

후처리

  1. additionwere added drop-wise
  2. temperatureThe mixture was heated for one hour
  3. temperatureunder reflux
  4. temperaturewas subsequently cooled to a temperature between 5° C. and 10° C
  5. additionwere added drop-wise at this temperature
  6. temperaturewas subsequently cooled again to a temperature between 5° C. and 10° C
  7. customAfter phase separation the batch
  8. extractionwas extracted twice with ether
  9. dry with materialdried over sodium sulphate
  10. customthe solvent was removed by distillation
  11. customThe residue obtained

출처 및 근거

ORD 기록
ord-b993ec200c4b4d7b8bdf662dfaa98480
출처 데이터셋
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05811582

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