(2-Aminoethoxy)(tert-butyl)dimethylsilane → N-[2-[tert-butyl(dimethyl)silyl]oxyethyl]oxetan-3-amine

HRID 2169330Notes

Reaction equation

HRID 2169330 reaction equation
[O:1]1[CH2:4][C:3](=O)[CH2:2]1.[Si:6]([O:13][CH2:14][CH2:15][NH2:16])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]>CO>[Si:6]([O:13][CH2:14][CH2:15][NH:16][CH:3]1[CH2:2][O:1][CH2:4]1)([C:9]([CH3:11])([CH3:12])[CH3:10])([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 529218(2-Aminoethoxy)(tert-butyl)dimethylsilaneHCID 150242543-Oxetanone

Product 1

HCID 86725969N-[2-[tert-butyl(dimethyl)silyl]oxyethyl]oxetan-3-amineYield 249.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of oxetan-3-one (1 g, 13.87 mmol) in methanol (40 mL) was added 2-(tert-butyl-dimethylsilanyloxy)-ethylamine (2.7 mg, 15.27 mmol). The mixture was stirred for 30 min at room temperature after cooling, Na(CN)BH3 was added portion-wise, followed by stirring at room temperature for 2 h. The reaction mixture was quenched with water, extracted with dichloromethane (3×30 mL). The organic part was concentrated, dried and purified by Combi-Flash column (eluted at 20-50% ethyl acetate in hexane) to get [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-oxetan-3-yl-amine (8 g) (1.5 g, 46.71%) as a light yellow oil.

Workup

  1. temperatureafter cooling
  2. stirringby stirring at room temperature for 2 h
  3. customThe reaction mixture was quenched with water
  4. extractionextracted with dichloromethane (3×30 mL)
  5. concentrationThe organic part was concentrated
  6. customdried
  7. custompurified by Combi-Flash column (eluted at 20-50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-985b792acda3451aacc14d5d2cc19991
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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