4-(N-Boc-amino)piperidine → tert-butyl 1-(2-(7-cyano-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-ylcarbamate

HRID 656892Notes

Reaction equation

HRID 656892 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([C:12]#[N:13])=[CH:7][CH:8]=2)[N:3]1[CH2:14][CH:15]=O.[C:17]([O:21][C:22]([NH:24][CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)(Cl)Cl.CO>[C:12]([C:6]1[CH:5]=[C:4]2[C:9]([CH:10]=[CH:11][C:2](=[O:1])[N:3]2[CH2:14][CH2:15][N:28]2[CH2:27][CH2:26][CH:25]([NH:24][C:22](=[O:23])[O:21][C:17]([CH3:19])([CH3:18])[CH3:20])[CH2:30][CH2:29]2)=[CH:8][CH:7]=1)#[N:13]

Participants

6

Reactant 3

HCID 7238334-(N-Boc-amino)piperidine2×HCID 5049666Sodium triacetoxyborohydride2×HCID 602002792-Oxo-1-(2-oxoethyl)-1,2-dihydroquinoline-7-carbonitrile

Product 1

HCID 60200429tert-butyl 1-(2-(7-cyano-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-ylcarbamateYield 99.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of 2-oxo-1-(2-oxoethyl)-1,2-dihydro-7-quinolinecarbonitrile (0.60 g, 2.8 mmol) and 4-t-butoxycarbonylaminopiperidine (0.68 g, 2.8 mmol) in chloroform (30 ml) and MeOH (20 ml) was stirred at 60° C. for 1 h. The mixture was then treated with NaBH(OAc)3 (1.8 g, 8.5 mmol), stirred at rt for 1 h, more 4-t-butoxycarbonylaminopiperidine (340 mg, 1.4 mmol) and NaBH(OAc)3 (1.2 g, 5.7 mmol) were then added and the reaction stirred at rt for 1 h. The solvents were then removed and the residue was subjected to column chromatography on silica gel eluting with 0-10% methanol-DCM to afford the desired compound (1.1 g, 98%).

Workup

  1. stirringthe reaction stirred at rt for 1 h
  2. customThe solvents were then removed

Sources & evidence

ORD record
ord-dfb1edab3dd74d09857f877287cc5687
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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