Sodium hydride → tert-Butyl {1-[2-(7-methoxy-2-oxo-3,4-dihydroquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

HRID 255184Notes

Reaction equation

HRID 255184 reaction equation
COC1C=C2C(CCC(=O)N2)=CC=1.[H-].[Na+].CS(OCCN1CCC(NC(OC(C)(C)C)=O)CC1)(=O)=O.[CH3:37][O:38][C:39]1[CH:48]=[C:47]2[C:42]([CH:43]=[CH:44][C:45](=[O:65])[N:46]2[CH2:49][CH2:50][N:51]2[CH2:56][CH2:55][CH:54]([NH:57][C:58](=[O:64])[O:59][C:60]([CH3:63])([CH3:62])[CH3:61])[CH2:53][CH2:52]2)=[CH:41][CH:40]=1>CC(C)=O.ClCCl.C(OCC)(=O)C>[CH3:37][O:38][C:39]1[CH:48]=[C:47]2[C:42]([CH2:43][CH2:44][C:45](=[O:65])[N:46]2[CH2:49][CH2:50][N:51]2[CH2:52][CH2:53][CH:54]([NH:57][C:58](=[O:64])[O:59][C:60]([CH3:61])([CH3:63])[CH3:62])[CH2:55][CH2:56]2)=[CH:41][CH:40]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 128994187-Methoxy-3,4-dihydroquinolin-2(1H)-one2×HCID 568344782-(4-((Tert-butoxycarbonyl)amino)piperidin-1-yl)ethyl methanesulfonate2×HCID 59371209tert-butyl {1-[2-(7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

Product 1

HCID 86642604tert-Butyl {1-[2-(7-methoxy-2-oxo-3,4-dihydroquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21584124Propan-2-one--dichloromethane (1/1)Solvent

Procedure

7-Methoxy-3,4-dihydroquinolin-2(1H)-one (Intermediate 33) (300 mg, 1.78 mmol) was deprotonated with sodium hydride (75 mg, 60% in oil, 1.86 mmol) and alkylated with 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}ethyl methanesulfonate (Intermediate 6) (2.03 mmol) as described for Intermediate 2. Chromatography on silica gel eluting with ethyl acetate and then acetone/dichloromethane (4:1) gave the product as a colorless oil, 559 mg (82%).

Sources & evidence

ORD record
ord-8d0d4910f65f4afc8a7982f2f141caad
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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