Methanol → HCID 131720621, compound

HRID 1599379Notes

Reaction equation

HRID 1599379 reaction equation
[CH2:1]=[CH:2][CH:3]1[CH:8]2[CH2:9][CH:10]([C@H:11]([OH:23])[C:12]3[CH:21]=[CH:20][N:19]=[C:18]4[C:13]=3[CH:14]=[C:15]([OH:22])[CH:16]=[CH:17]4)[N:5]([CH2:6][CH2:7]2)[CH2:4]1.Br[CH2:25][CH2:26][CH2:27][N:28]1[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]2[C:29]1=[O:38].C(=O)([O-])[O-].[K+].[K+].CO>CC(C)=O.C1OCCOCCOCCOCCOCCOC1>[OH:23][C@@H:11]([C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[C:15]([O:22][CH2:25][CH2:26][CH2:27][N:28]3[C:32](=[O:33])[C:31]4[C:30](=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:29]3=[O:38])[CH:14]=2)[N:19]=[CH:20][CH:21]=1)[C@@H:10]1[N:5]2[CH2:6][CH2:7][C@H:8]([C@@H:3]([CH:2]=[CH2:1])[CH2:4]2)[CH2:9]1

Participants

7

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 51196O-Desmethylquinidine

Product 1

HCID 131720621HCID 131720621, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 180AcetoneSolvent

Procedure

A mixture of 6-hydroxycinchonine (1) (2.5 g, 8.06 mmol), N-(3-bromopropyl)phthalimide (2.16 g, 8.06 mmol), anhydrous potassium carbonate (1.3 g, 9.4 mmol) and 18-crown-6 (5 mg) in 75 ml of dry acetone was allowed to reflux for 16 h under argon atmosphere. The reaction was cooled to room temperature and 30 ml of methanol was added to make a homogeneous solution. The resulting solution was concentrated and the residue was partially purified on silica gel column chromatography using 5% methanol in chloroform as the eluent. This product was repurified on silica gel column chromatography using 10% methanol in chloroform and yielded 1.08 g (2.17 mmol, 27%) of (11) as off-white solids. MS, IR and NMR data confirmed compound identity.

Workup

  1. temperatureto reflux for 16 h under argon atmosphere
  2. concentrationThe resulting solution was concentrated
  3. customthe residue was partially purified on silica gel column chromatography
  4. customThis product was repurified on silica gel column chromatography

Sources & evidence

ORD record
ord-bc5838df03624b8caf7e2f240405885f
Source dataset
uspto-grants-1998_04
Patent number
US05741715

Reaction notes

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