Water → Tert-butyl [4-(6-methoxy-quinolin-4-yloxymethyl)-cyclohexyl]carbamate

HRID 1354228Notes

Reaction equation

HRID 1354228 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:9]=[C:8]2[OH:15].[C:16]([O:20][C:21]([NH:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([CH2:30]OS(C)(=O)=O)[CH2:26][CH2:25]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].O>CN(C=O)C.C(OCC)(=O)C>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:9]=[C:8]2[O:15][CH2:30][CH:27]1[CH2:26][CH2:25][CH:24]([NH:23][C:21](=[O:22])[O:20][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:29][CH2:28]1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 178453973HCID 178453973, compoundHCID 178487890HCID 178487890, compound

Product 1

HCID 58603138Tert-butyl [4-(6-methoxy-quinolin-4-yloxymethyl)-cyclohexyl]carbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

NaH dispersion (55% in mineral oil, 88 mg, 2 mmol) was added to a suspension of 6-methoxy-4-hydroxyquinoline (350 mg, 2 mmol) in DMF (4 ml) and stirred at room temperature until a solution formed. trans-Methanesulphonic acid 4-tert-butoxycarbonylaminocyclohexylmethyl ester (635 mg, 2 mmol) was added and the reaction mixture was stirred overnight at 80° C. Water was added to the mixture and extraction was carried out with ethyl acetate. Organic extracts washed with water, dried over Na2SO4 and concentrated. The crude product was purified by chromatography on silica gel (DCM/MeOH 9:1).

Workup

  1. customformed
  2. stirringthe reaction mixture was stirred overnight at 80° C
  3. washOrganic extracts washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was purified by chromatography on silica gel (DCM/MeOH 9:1)

Sources & evidence

ORD record
ord-4e4ad4bcad434403aae8e92531f49556
Source dataset
uspto-grants-2007_05
Patent number
US07223776B2

Reaction notes

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