Sodium Bicarbonate → tert-butyl (1-(2-(7-methoxy-2-oxo-1,8-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

HRID 656898Notes

Reaction equation

HRID 656898 reaction equation
[CH3:1][O:2][C:3]1[N:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH:14]=C)=[CH:5][CH:4]=1.I([O-])(=O)(=O)=O.[Na+].[NH:23]1[CH2:28][CH2:27][CH:26]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:25][CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>O1CCOCC1.O.[Cl-].[Na+].O.ClCCl.CO.[Os](=O)(=O)(=O)=O.ClCCl.O>[CH3:1][O:2][C:3]1[N:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH2:14][N:23]2[CH2:24][CH2:25][CH:26]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:33])[CH3:35])[CH2:27][CH2:28]2)=[CH:5][CH:4]=1

Participants

12

Reactant 5

HCID 516892Sodium BicarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 23667635Sodium periodateHCID 688163437-(Methyloxy)-1-(2-propen-1-yl)-1,8-naphthyridin-2(1H)-one

Product 1

HCID 57815232tert-butyl (1-(2-(7-methoxy-2-oxo-1,8-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Reagents, catalysts & solvents 6

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolventHCID 218864351,4-Dioxane--water (1/1)SolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 7-(methyloxy)-1-(2-propen-1-yl)-1,8-naphthyridin-2(1H)-one (240 mg, 1.1 mmol) in 1,4-dioxane/water (12 ml/20 ml) was treated with osmium tetroxide solution (4% in water, 1 ml) followed by sodium periodate (2.1 g, 10 mmol). After 30 minutes more water (15 ml) was added. After a further 1 hour the mixture was diluted with an equal mixture of brine and extracted twice with ethyl acetate. The dried extracts were evaporated to give a yellow oil. This was dissolved in dichloromethane/methanol (6 ml/0.6 ml) and treated with 1,1-dimethylethyl 4-piperidinylcarbamate (240 mg, 1.2 mmol) then sodium triacetoxyborohydride (626 mg, 3 mmol). After 2 hours the mixture was treated with saturated aqueous sodium bicarbonate and dichloromethane. The organic extract was added to a silica column, eluting with 0-100% ethyl acetate in hexane then 0-20% methanol in ethyl acetate, affording a brown foam (320 mg, 72% over 2 steps).

Workup

  1. extractionextracted twice with ethyl acetate
  2. customThe dried extracts were evaporated
  3. customto give a yellow oil
  4. extractionThe organic extract
  5. additionwas added to a silica column
  6. washeluting with 0-100% ethyl acetate in hexane
  7. custom0-20% methanol in ethyl acetate, affording a brown foam (320 mg, 72% over 2 steps)

Sources & evidence

ORD record
ord-b1e3e0f133454b77a10132fb6ea5cb6c
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

Loading…