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

HRID 500053

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HRID 500053 반응식
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

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

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온도
-20 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-9c287d615b44465c8b90e329552ec1cf
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767860B2

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