Imidazole → 3-(Tert-butyldiphenylsilyloxy)butan-1-amine

HRID 249850

Reaction equation

HRID 249850 reaction equation
[OH:1][CH:2](CC)[CH2:3]N.[Si:7](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.N1[CH:29]=[CH:28][N:27]=C1>CN(C=O)C>[Si:7]([O:1][CH:2]([CH3:3])[CH2:29][CH2:28][NH2:27])([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 261071-Amino-2-butanolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 588420273-(Tert-butyldiphenylsilyloxy)butan-1-amineYield 181.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-hydroxybutylamine (4.00 g, 44.87 mmol) in anhydrous DMF (25 mL) was added tert-butyldiphenylsilylchloride (16.9 mL, 66.19 mmol) and imidazole (9.16 g, 13.46 mmol). The reaction mixture was stirred at room temperature for 2 days, then concentrated under reduced pressure, and diluted with CH2Cl2 (150 mL). The organics were washed with 5% aqueous NaHCO3 solution (50 mL), brine (50 mL), dried (MgSO4), filtered, and concentrated. The crude material was purified by column chromatography (0 to 100% EtOAc in hexane) to give 3-(tert-butyldiphenylsilyloxy)butan-1-amine (8.00 g, 54%) as a white solid. 1H NMR and MS consistent.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiondiluted with CH2Cl2 (150 mL)
  3. washThe organics were washed with 5% aqueous NaHCO3 solution (50 mL), brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by column chromatography (0 to 100% EtOAc in hexane)

Sources & evidence

ORD record
ord-f5b564884e16498d909f4bcd7ddd4f55
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Linked notes

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