Reserpine → HCID 21931803, compound

HRID 1244030Notes

Reaction equation

HRID 1244030 reaction equation
C([O-])(=[O:3])C.[NH4+].CO[C@@H]1[C@@H](C(OC)=O)[C@@H]2[C@@H](CN3[C@H](C2)[C:17]2[NH:26][C:27]4[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:28]=4[C:16]=2[CH2:15][CH2:14]3)C[C@H]1OC(C1C=C(OC)C(OC)=C(OC)C=1)=O>C(#N)C>[CH3:34][O:33][C:31]1[CH:32]=[C:27]2[C:28]([CH2:16][CH2:15][C:14](=[O:3])[N:26]2[CH3:17])=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 5770ReserpineHCID 517165Ammonium Acetate

Product 1

HCID 21931803HCID 21931803, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under nitrogen, combined 3.2 g of 7-Hydroxy-3,4-dihydro-1H-quinolin-2-one (0.0196 mol) with 25 ml of THF. Added 5.1 g of potassium t-butoxide (0.0451 mol) and stirred for 1.25 hours. Added 4.3 ml of dimethyl sulfate (0.0451 mol), followed by 10 ml of THF and stirred overnight. The reaction mixture was diluted with EtOAc and extracted three times with H2O, dried (MgSO4), and evaporated under reduced pressure. Purified by chromatography on Biotage Flash 40, eluting with 3:1 Hexanes/EtOAc to give 1.7 g of white solid (45%). 1H NMR (400 MHz, CDCl3) δ 2.62 (2H, q, J=5.39 Hz), 2.83 (2H, q, J=6.85 Hz), 3.32 (3H, s), 3.81 (3H, s), 6.53 (1H, d, J=2.49 Hz), 6.54 (1H, d, J=1.87 Hz), 7.05 (1H, d, J=7.68 Hz). M/z (APCI+) 192.1 (M+1). HPLC (aqueous 200 mM ammonium acetate buffer/acetonitrile gradient, 3.0 ml/min, Hewlett Packard ODS Hypersil 5 uM, 125×4 mm column) 4.068.

Sources & evidence

ORD record
ord-4b816e3225774ba4a96cd05146647b9c
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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