Carbon Dioxide → HCID 69134515, 화합물

HRID 917686노트

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HRID 917686 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][Si](C(C)(C)C)(C)C)[CH:6]=[CH:5]2.C([Li])CCC.C(=O)=O.[CH2:28]([O:35][CH:36]1[CH2:41][CH2:40][C:39](=[O:42])[CH:38]([CH2:43][N:44]([CH3:46])[CH3:45])[CH2:37]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1COCC1.CCCCCC.O>[CH2:28]([O:35][CH:36]1[CH2:41][CH2:40][C:39]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]3)([OH:42])[CH:38]([CH2:43][N:44]([CH3:46])[CH3:45])[CH2:37]1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

참가 물질

8

반응물 4

HCID 280Carbon DioxideHCID 10999837HCID 10999837, 화합물HCID 134730832-Bromo-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]naphthaleneHCID 178418339Butyllithium

생성물 1

HCID 69134515HCID 69134515, 화합물수율 70.9%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

3.87 g (6-bromonaphthalen-2-yloxy)-tert.-butyldimethylsilane were dissolved in 19 ml THF p.a., 6.0 ml 1.6 M butyl lithium solution in hexane added dropwise with dry ice cooling, briefly stirred, then a solution of 2.00 g 4-benzyloxy-2-dimethylaminomethylcyclohexanone in 20 ml THF p.a. added dropwise and stirred for 1 hour while slowly heating. For working up, 4 ml water were added to the ice bath, the organic phase separated, the aqueous phase extracted twice with diethyl ether, the combined organic phases dried by sodium sulphate, filtered and concentrated. The crude product obtained (5.00 g) was chromatographed with ethyl acetate/methanol (V/V=1:1) on silica gel. 2.20 g 6-(4-benzyloxy-2-dimethylaminomethyl-1-hydroxy-cyclohexyl)-naphthalen-2-ol were obtained and converted into the corresponding hydrochloride (1.33 g) in the same way as in AAV 1.

후처리

  1. additionadded dropwise
  2. stirringstirred for 1 hour
  3. temperaturewhile slowly heating
  4. customthe organic phase separated
  5. extractionthe aqueous phase extracted twice with diethyl ether
  6. dry with materialthe combined organic phases dried by sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product obtained (5.00 g)
  10. customwas chromatographed with ethyl acetate/methanol (V/V=1:1) on silica gel

출처 및 근거

ORD 기록
ord-9a8e8e931b6d4e308bb77af68f3a02c1
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07273952B2

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