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

HRID 1644305Notes

Reaction equation

HRID 1644305 reaction equation
COC1C=C2C(CCC(=O)N2)=CC=1.[H-].[Na+].CS(OCCN1CCC(NC(OC(C)(C)C)=O)CC1)(=O)=O.[C:37]([O:41][C:42](=[O:65])[NH:43][CH:44]1[CH2:49][CH2:48][N:47]([CH2:50][CH2:51][N:52]2[C:61]3[C:56](=[CH:57][CH:58]=[C:59]([O:62][CH3:63])[CH:60]=3)[CH:55]=[CH:54][C:53]2=[O:64])[CH2:46][CH2:45]1)([CH3:40])([CH3:39])[CH3:38]>CC(C)=O.ClCCl.C(OCC)(=O)C>[C:37]([O:41][C:42](=[O:65])[NH:43][CH:44]1[CH2:45][CH2:46][N:47]([CH2:50][CH2:51][N:52]2[C:61]3[C:56](=[CH:57][CH:58]=[C:59]([O:62][CH3:63])[CH:60]=3)[CH2:55][CH2:54][C:53]2=[O:64])[CH2:48][CH2:49]1)([CH3:40])([CH3:38])[CH3:39]

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-a05727e1522d45469384cdf0d7c4c246
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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