Sodium Sulfate → tert-Butyl {1-[2-(7-fluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

HRID 657096Notes

Reaction equation

HRID 657096 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:15])[N:9]2[CH2:12][CH:13]=O)=[CH:4][CH:3]=1.[NH:16]1[CH2:21][CH2:20][CH:19]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:18][CH2:17]1.[O-]S([O-])(=O)=O.[Na+].[Na+].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO.C(Cl)Cl>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:15])[N:9]2[CH2:12][CH2:13][N:16]2[CH2:17][CH2:18][CH:19]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[CH2:20][CH2:21]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 24436Sodium SulfateHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 86635311(7-Fluoro-2-oxo-1(2H)-quinolinyl)acetaldehyde

Product 1

HCID 86635312tert-Butyl {1-[2-(7-fluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamateYield 72.2%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

(7-Fluoro-2-oxo-1(2H)-quinolinyl)acetaldehyde (0.50 g, 2.41 mmol) (for a preparation see Example 88(a)) was combined with 1,1-dimethylethyl 4-piperidinylcarbamate (0.48 g, 2.41 mmol) in 1:1 MeOH/DCM (20 mL). Excess Na2SO4 was added as a drying agent and the solution was stirred at ambient temperature for 16 h. NaBH(OAc)3 (1.53 g, 7.23 mmol) was added and the reaction was stirred an additional 2 h. The solution was concentrated onto silica gel under vacuum and the crude residue purified by column chromatography (silica gel) using a DCM/DCM-MeOH—NH4OH (90:10:1) gradient to yield the desired product as a yellow solid (0.678 g, 72%).

Workup

  1. stirringthe reaction was stirred an additional 2 h
  2. concentrationThe solution was concentrated onto silica gel under vacuum
  3. customthe crude residue purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-cac390c7f9d942d5bad03a44b6185d8c
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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