Реакция #6063

Уравнение реакции

acetic acid

K-Selectride

N-(Benzyloxycarbonyl)-3-amino-1-cyclobutanone

potassium tri-sec-butylborohydride

→

title compound

Выход 63.0%

N-(Benzyloxycarbonyl)-3-amino-1-cyclobutanol

Выход 63.0%

Растворители

THF

THF

THF

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirring
2. 2
   ФильтрацияThe reaction mixture was then filtered through Celite
3. 3
   Фильтрацияfilter aid
4. 4
   Концентрированиеconcentrated in vacuo
5. 5
   workup.DISSOLUTIONThe residue (3.1 g) was dissolved in ~10 mL of methylene chloride
6. 6
   Другоеpurified on a 1.5×45 cm silica gel column
7. 7
   Промывкаeluted @ 5 psi with 250 mL of acetone:hexane (1:2 v/v)

Методика

N-(Benzyloxycarbonyl)-3-amino-1-cyclobutanone (3.51 g, 16.0 mmol) from Step A was dissolved in 100 mL of THF and the THF solution was cooled to -78° C. with stirring under a nitrogen atmosphere. To the solution was added 17.6 mL (17.6 mmol) of potassium tri-sec-butylborohydride (sold by Aldrich Chemical Company as a 1M solution in THF under the registered trademark K-Selectride®) and stirring was continued for 10 minutes. The reaction mixture was allowed to warm to 0° C. and then quenched with 1.16 mL (1 equivalent) of glacial acetic acid. The reaction mixture was then filtered through Celite filter aid and concentrated in vacuo. The residue (3.1 g) was dissolved in ~10 mL of methylene chloride and purified on a 1.5×45 cm silica gel column eluted @ 5 psi with 250 mL of acetone:hexane (1:2 v/v), followed by 200 mL of acetone:hexane (1:1 v/v) to give 2.22 g (63% yield) of the title compound; MS DCI-NH3M/Z: 222 (M+H)+, 239 (M+NH4)+ ; 1H NMR (CD3OD) δ 1.81 (m, 2H), 2.62 (m, 2H), 3.60 (m, 1H), 3.90 (m, 1H), 5.09 (s, 2H), 7.25-7.40 (m, 5H).

Источник