反応 #6063

反応方程式

acetic acid

K-Selectride

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

potassium tri-sec-butylborohydride

→

title compound

収率 63.0%

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

収率 63.0%

溶媒

THF

THF

THF

反応条件

後処理

1. 1
   workup.STIRRINGstirring
2. 2
   ろ過The reaction mixture was then filtered through Celite
3. 3
   ろ過filter aid
4. 4
   濃縮concentrated in vacuo
5. 5
   workup.DISSOLUTIONThe residue (3.1 g) was dissolved in ~10 mL of methylene chloride
6. 6
   その他purified on a 1.5×45 cm silica gel column
7. 7
   洗浄eluted @ 5 psi with 250 mL of acetone:hexane (1:2 v/v)

実験手順

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).

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