Imidazole → N-[2-(benzyloxy)-ethyl]-4-{[tert-butyl(dimethyl)silyl]oxy}butan-1-amine

HRID 2426466Notes

Reaction equation

HRID 2426466 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6].[C:7]([Si:11](Cl)([CH3:13])[CH3:12])([CH3:10])([CH3:9])[CH3:8].N1C=CN=C1.[CH2:20]([O:27][CH2:28][CH:29]=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.ClC(Cl)C>[CH2:20]([O:27][CH2:28][CH2:29][NH:6][CH2:5][CH2:4][CH2:3][CH2:2][O:1][Si:11]([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:13])[CH3:12])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

8

Reactant 5

HCID 795ImidazoleHCID 258684-Amino-1-butanolHCID 28928tert-Butyldimethylsilyl chlorideHCID 108989(Phenylmethoxy)acetaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 66997788N-[2-(benzyloxy)-ethyl]-4-{[tert-butyl(dimethyl)silyl]oxy}butan-1-amine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 4-hydroxybutylamine (4.0 g, 44.9 mmol), tert-butyldimethyl-silyl chloride (7.4 g, 49.3 mmol) and imidazole (6.7 g, 98.7 mmol) in dichloromethane (150 mL) was stirred at room temperature for 2 hours. The product mixture was washed successively with aqueous NaHCO3, water, and brine. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. This intermediate silylated aminoalcohol was used without further purification. To a mixture of the amine (1.0 g, 4.9 mmol) and benzyloxyacetaldehyde (0.74 g, 4.9 mmol) in dichloroethane (15 mL) at room temperature, sodium triacetoxyborohydride (1.3 g, 6.3 mmol) was added. The reaction mixture was concentrated under vacuum. The residue was partitioned between ethyl acetate and aqueous sodium carbonate. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 2% methanol in dichloromethane. Collection and concentration of appropriate fractions afforded the title silyloxybutyl-amine.

Workup

  1. washThe product mixture was washed successively with aqueous NaHCO3, water, and brine
  2. extractionThe organic extract
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThis intermediate silylated aminoalcohol was used without further purification
  7. concentrationThe reaction mixture was concentrated under vacuum
  8. customThe residue was partitioned between ethyl acetate and aqueous sodium carbonate
  9. extractionThe organic extract
  10. dry with materialwas dried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under vacuum
  13. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-9c1ff5fcae91454e9447df3a0868d7a3
Source dataset
uspto-grants-2011_06
Patent number
US07968564B2

Reaction notes

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