Potassium Carbonate → HCID 131720616, compound

HRID 1599372Notes

Reaction equation

HRID 1599372 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.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][CH2:32][CH2:33][C:34]#[N:35]>CC(C)=O.CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[OH:23][C@@H:11]([C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[C:15]([O:22][CH2:31][CH2:32][CH2:33][C:34]#[N:35])[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 3

HCID 11430Potassium CarbonateHCID 214124-BromobutyronitrileHCID 51196O-Desmethylquinidine

Product 1

HCID 131720616HCID 131720616, compoundYield 94.3%

Reagents, catalysts & solvents 3

HCID 2855718-Crown-6CatalystHCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 400 mg (1.2 mmol) of 6-hydroxycinchonane (1) in 25 ml of anhydrous acetone (dried and distilled over potassium carbonate) and 5 ml of anhydrous dimethylformamide was added 267 mg (1.93 mmol) of anhydrous potassium carbonate followed by 129 ml (0.87 mmol) of 4-bromobutyronitrile and a catalytic amount (3 mg) of 18-crown-6. The reaction mixture was heated to reflux for 18 h, cooled and filtered. The filtrate was concentrated under reduced pressure and redissolved in 200 ml of chloroform. The organic layer was washed with 2×50 ml of 5% aqueous sodium hydroxide, washed with brine, dried using anhydrous magnesium sulfate and yielded 310 mg (0.82 mmol, 66%) of (9S)-4-[(9-hydroxycinchonan-6'-yl)oxy]butanenitrile (2) as pale yellow solids. MS, IR and NMR data confirmed the identity of the compound.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 18 h
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. dissolutionredissolved in 200 ml of chloroform
  7. washThe organic layer was washed with 2×50 ml of 5% aqueous sodium hydroxide
  8. washwashed with brine
  9. customdried

Sources & evidence

ORD record
ord-e8cce4fa393d4fd1a3c64059dad37b66
Source dataset
uspto-grants-1998_04
Patent number
US05741715

Reaction notes

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