Water → (3RS,4R)-4-(Trityl-amino)-hexan-3-ol

HRID 729566

반응식

HRID 729566 반응식
[C:1]([NH:20][C@H:21]([CH2:24][CH3:25])[CH:22]=[O:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]([Mg]Br)[CH3:27].O>CCOCC>[C:1]([NH:20][C@H:21]([CH2:24][CH3:25])[CH:22]([OH:23])[CH2:26][CH3:27])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 57714153(R)-2-(Trityl-amino)-butyraldehydeHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 57714154(3RS,4R)-4-(Trityl-amino)-hexan-3-ol

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
-78 °C

실험 절차

To a stirred solution of (R)-2-(trityl-amino)-butyraldehyde (1.5 g, 1 eq, 4.53 mmol) in Et2O (150 mL) under an argon atmosphere at −78° C., was added ethylmagnesium bromide (3 M in Et20, 1.51 mL, 1 eq, 4.53 mmol) dropwise. The solution was stirred at −78° C. for 2 h, then allowed to warm to room temperature over 16 h. The mixture was recooled to 0° C., H2O (150 mL) added, and the organic phase separated. The aqueous phase was extracted with more Et2O (2×50 mL), and the combined organic phase washed with brine (50 mL), dried (MgSO4) and evaporated in vacuo. The residue was purified by silica gel column chromatography, eluted with hexane:ether (90:10) to afford the title compound as a light yellow oil. Yield: 1.13 g (69%). (57% de 3S,4R: 43% de 3R,4R). 1H-NMR (d6-DMSO, 250 MHz): δ0.45 & 0.69 (t & m, 6H, J=7.43 Hz, —NHCH(CH2CH3)CH(CH2CH3)OH), 1.12-1.29 (m, 4H, —NHCH (CH2CH3)CH(CH2CH3)OH), 2.16 (m, 1H, —NHCH(CH2CH3)CH(CH2CH3)OH), 2.54 (m, 1H, —NHCH(CH2CH3)CH(CH2CH3)OH), 3.21-3.40 (m, 1H, —NHCH(CH2CH3) CH(CH2 CH3)OH), 4.29+4.39 (2×d, 1H, J=4.42 & 5.37 Hz, —NHCH(CH2CH3)CH (CH2CH3)OH), 7.15-7.52 (m, 15H, 3×Ph).

후처리

  1. temperatureto warm to room temperature over 16 h
  2. customwas recooled to 0° C.
  3. customthe organic phase separated
  4. extractionThe aqueous phase was extracted with more Et2O (2×50 mL)
  5. washthe combined organic phase washed with brine (50 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customThe residue was purified by silica gel column chromatography
  9. washeluted with hexane:ether (90:10)

출처 및 근거

ORD 기록
ord-b4f4fb1e3f574a848bb95a04792df1d3
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582642B2

연결된 노트

불러오는 중…