3,4-dihydro-2H-pyran → 8-(Benzyloxy)-5-[(1R)-2-bromo-1-(tetrahydro-2H-pyran-2-yloxy)ethyl]quinolin-2(1H)-one

HRID 749227Notes

Reaction equation

HRID 749227 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([OH:23])[CH2:21][Br:22])=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1.[O:41]1[CH:46]=[CH:45][CH2:44][CH2:43][CH2:42]1>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:23][CH:42]2[CH2:43][CH2:44][CH2:45][CH2:46][O:41]2)[CH2:21][Br:22])=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 115308845-((1R)-2-bromo-1-hydroxyethyl)-8-phenylmethoxy-1H-quinolin-2-one

Product 1

HCID 115833968-(Benzyloxy)-5-[(1R)-2-bromo-1-(tetrahydro-2H-pyran-2-yloxy)ethyl]quinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

A suspension of 8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one (100 mg) and pyridinium tosylate (14 mg) in dry DCM (2 ml) was treated with 2,3-dihydropyran (61.2 μl) and stirred at 22° C. for 18 h. The reaction mixture was concentrated in vacuo and purified by chromatography (Hexane-EtOAc 2:1, biotage) to give the title compound (77 mg). Rf [EtOAc-Hexane (1:1)] 0.54

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by chromatography (Hexane-EtOAc 2:1, biotage)

Sources & evidence

ORD record
ord-89c5820dca914474a8f68d9bad107114
Source dataset
uspto-grants-2008_07
Patent number
US07402598B2

Reaction notes

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