Water → HCID 68677158, compound

HRID 968630Notes

Reaction equation

HRID 968630 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[C:10]([O:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]Br)=[O:16])([CH3:13])([CH3:12])[CH3:11].O>CN(C)C=O>[C:10]([O:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 79713-HydroxypyridineHCID 24758Sodium hydrideHCID 16211353tert-Butyl (6-bromohexyl)carbamate

Product 1

HCID 68677158HCID 68677158, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

3-Hydroxypyridine (262 mg) was added to a suspension of 60% sodium hydride (128 mg) in N,N-dimethylformamide (5 ml) and the mixture was stirred at 60° C. for 30 minutes. After cooling in ice a solution of N-(tert-butoxycarbonyl)-6-bromo-hexylamine (770 mg) (Helv. Chim. Acta 76 891 (1993) in N,N-dimethylformamide (3 ml) was added dropwise and stirring was continued overnight at room temperature. Ice and water were added and the mixture was extracted three times with diethyl ether. The organic phases were washed with saturated sodium chloride, dried and evaporated to leave a yellow oil which after purification by chromatography on silica gel with diethyl ether as eluent gave the desired compound as a colourless oil.

Workup

  1. stirringstirring
  2. waitwas continued overnight at room temperature
  3. extractionthe mixture was extracted three times with diethyl ether
  4. washThe organic phases were washed with saturated sodium chloride
  5. customdried
  6. customevaporated
  7. customto leave a yellow oil which
  8. customafter purification by chromatography on silica gel with diethyl ether as eluent

Sources & evidence

ORD record
ord-22299cfaccf744fea4df5922e040d4a7
Source dataset
uspto-grants-2007_12
Patent number
US07304066B2

Reaction notes

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