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

HRID 1432397노트

반응식

HRID 1432397 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

실험 절차

To a stirred solution of (R)-2-(trityl-amino)-butyraldehyde (1.5 g, 1 eq, 4.53 mmol) in ether (150 mL) under an argon atmosphere at −78° C., was added ethylmagnesium bromide (3 M in ether, 1.51 mL, 1 eq, 4.53 mmol) dropwise. The solution was sired at −78° C. for 2 h, then allowed to warm to room temperature over 16 h. The mixture was re-cooled to 0° C., H2O (150 mL) added, and the organic phase separated. The aqueous phase was extracted with more ether (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% A de 3S,4R: 43% de 3R,4R). 1H-NMR (d6-DMSO, 250 MHz): δ 0.45+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(CH2CH3)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×Bz).

후처리

  1. temperatureThe mixture was re-cooled to 0° C.
  2. customthe organic phase separated
  3. extractionThe aqueous phase was extracted with more ether (2×50 mL)
  4. washthe combined organic phase washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluted with hexane:ether (90:10)

출처 및 근거

ORD 기록
ord-d0f801128dfb48acb41cbc712ba966dd
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612079B2

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