Chloroform → tert-butyl {1-[2-(7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

HRID 656882Notes

Reaction equation

HRID 656882 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH:14]=O)=[CH:5][CH:4]=1.[NH:17]1[CH2:22][CH2:21][CH:20]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:19][CH2:18]1.C(Cl)(Cl)Cl.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH2:14][N:17]2[CH2:18][CH2:19][CH:20]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH2:21][CH2:22]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 59397833(7-methoxy-2-oxoquinolin-1(2H)-yl)acetaldehyde

Product 1

HCID 59371209tert-butyl {1-[2-(7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamateYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[7-(Methyloxy)-2-oxo-1(2H)-quinolinyl]acetaldehyde (2.31 g, 10.65 mmol) and 1,1-dimethylethyl 4-piperidinylcarbamate (3.15 g, 15.98 mmol) were stirred in a 1:1 mixture of chloroform and methanol (140 ml) for 1 h at rt under argon. This mixture was then treated with NaBH(OAc)3 (10.16 g, 47.93 mmol) and stirred for a further 45 mins. The solvents were then removed from the reaction and crude residues purified by column chromatography on silica gel using a 0-35% MeOH/DCM gradient, to give the desired product (2.0 g; 47%).

Workup

  1. customThe solvents were then removed from the reaction and crude residues
  2. custompurified by column chromatography on silica gel using a 0-35% MeOH/DCM gradient

Sources & evidence

ORD record
ord-ff825b807e9c4c4fb15177fdf8f01624
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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