Butanal → (R)-2-(N-Phenyl-aminooxy)-butan-1-ol

HRID 500053

反応式

HRID 500053 の反応式
N1CCC[C@H]1C(O)=O.[CH:9](=[O:13])[CH2:10][CH2:11][CH3:12].[N:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15].[BH4-].[Na+].P([O-])([O-])([O-])=O>C(#N)C.C(OCC)(=O)C.CO>[C:16]1([NH:14][O:15][C@H:10]([CH2:11][CH3:12])[CH2:9][OH:13])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

9

反応物 5

HCID 261ButanalHCID 1061PhosphateHCID 11473NitrosobenzeneHCID 145742L-ProlineHCID 4311764Sodium borohydride

生成物 1

HCID 11816230(R)-2-(N-Phenyl-aminooxy)-butan-1-ol収率 43%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-20 °C

実験手順

At about −20° C., L-proline (4 g, 34.8 mmol) was added to solution of n-butyraldehyde (25 mL, 278 mmol) and nitrosobenzene (15 g, 140 mmol) in acetonitrile (300 mL). The mixture was stirred at about −20° C. for about 48 hours, methanol (50 mL) and sodium borohydride (16 g, 432 mmol) were added, the mixture was stirred for about 10 minutes, and phosphate buffer was added. Following standard extractive workup with ethyl acetate, the crude product was purified by column chromatography with silica gel (petroleum ether-ethyl acetate =5:1, v:v, elution) to afford the title product (10.8 g, 43%). 1H NMR (300 MHz, CDCl3) δ 7.30-7.25 (m, 2H), 7.01-6.96 (m, 3H), 3.90-3.74 (m, 3H), 1.75-1.57 (m, 2H), 1.02 (t, J=7.8 Hz, 3H); LC-MS: m/z=182 (M+H)+.

後処理

  1. stirringthe mixture was stirred for about 10 minutes
  2. customthe crude product was purified by column chromatography with silica gel (petroleum ether-ethyl acetate =5:1, v:v, elution)

出典と根拠

ORDレコード
ord-9c287d615b44465c8b90e329552ec1cf
出典データセット
uspto-grants-2010_08
特許番号
US07767860B2

関連ノート

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