Carbon Dioxide → HCID 69134515, compound

HRID 917686Notes

Reaction equation

HRID 917686 reaction equation
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

Participants

8

Reactant 4

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

Product 1

HCID 69134515HCID 69134515, compoundYield 70.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9a8e8e931b6d4e308bb77af68f3a02c1
Source dataset
uspto-grants-2007_09
Patent number
US07273952B2

Reaction notes

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