Sodium Sulfate → HCID 86635347, compound

HRID 657066Notes

Reaction equation

HRID 657066 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)=[N:5][CH:4]=1.[NH:17]1[CH2:22][CH2:21][CH2:20][C@@H:19]([CH2:23][NH:24][C:25](=[O:34])[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:18]1.[O-]S([O-])(=O)=O.[Na+].[Na+].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO.C(Cl)(Cl)Cl>[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[CH2:22][CH2:21][CH2:20][C@@H:19]([CH2:23][NH:24][C:25](=[O:34])[O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:18]2)=[N:5][CH:4]=1

Participants

6

Reactant 4

HCID 24436Sodium SulfateHCID 5049666Sodium triacetoxyborohydrideHCID 44828666(R)-benzyl piperidin-3-ylmethylcarbamateHCID 57815194(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde

Product 1

HCID 86635347HCID 86635347, compound

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

To a solution of [7-(methoxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]acetaldehyde (as the methyl hemiacetal) (0.250 g, 1.15 mmol) in 1:1 (MeOH/CHCl3) (25 mL) were added phenylmethyl [(3R)-3-piperidinyl-methyl]carbamate (0.210 g, 0.90 mmol) and Na2SO4 (0.100 g) and the resulting solution stirred at ambient temperature for 18 hours. Na(OAc)3BH (0.57 g, 2.7 mmol) was added and solution stirred an additional 2 hours. The reaction mixture was concentrated onto silica gel and chromatographed on a silica gel column) [0-100% Hexanes/EtOAc] to yield a colorless oil. (0.207 g, 51%) LCMS: m/z 451 (M+H)+.

Workup

  1. stirringsolution stirred an additional 2 hours
  2. concentrationThe reaction mixture was concentrated onto silica gel
  3. customchromatographed on a silica gel column) [0-100% Hexanes/EtOAc]
  4. customto yield a colorless oil

Sources & evidence

ORD record
ord-93e77e39ea7940a7a081d892b46d1d40
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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