1,2-Ethanedithiol → 2-(2-(1-(Benzyloxycarbonyl)piperidin-4-yl)ethyl)-2-phenyl-1,3-dithiolane

HRID 278222노트

반응식

HRID 278222 반응식
B(F)(F)F.C(O)(=O)C.[CH2:9]([SH:12])[CH2:10][SH:11].[CH2:13]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([CH2:29][CH2:30][C:31](=O)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:25][CH2:24]1)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl.CCOCC>[CH2:13]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([CH2:29][CH2:30][C:31]2([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[S:12][CH2:9][CH2:10][S:11]2)[CH2:25][CH2:24]1)=[O:22])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

참가 물질

6

반응물 3

HCID 109021,2-EthanedithiolHCID 61423Hydrogen (acetato-O)trifluoroborate(1-)HCID 181874541-(Benzyloxycarbonyl)-4-(3-oxo-3-phenylpropyl)piperidine

생성물 1

HCID 181877152-(2-(1-(Benzyloxycarbonyl)piperidin-4-yl)ethyl)-2-phenyl-1,3-dithiolane수율 92.7%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

Boron trifluoride-acetic acid complex (BF3.2-CH3CO2H, 0.370 mL, 501 mg, 2.67 mmol) was added to a solution of 1,2-ethanedithiol (0.440 mL, 494 mg, 5.25 mmol) and (1-(benzyloxycarbonyl)-4-(3-oxo-3-phenylprop-1-yl)piperidine (930 mg, 2.65 mmol) in methylene chloride (4.0 mL) at rt. After 6 h, the mixture was diluted with ether (50 mL) and washed with saturated aq. sodium bicarbonate (2×25 mL), 2.5 N aq. NaOH (25 mL), and saturated aq. brine (25 mL). The organic layer was dried (sodium sulfate), decanted, and evaporated. The crude product was purified by FC, eluting with 10% ethyl acetate in hexane, to give 1.05 g of the title compound as a colorless liquid.

후처리

  1. customat rt
  2. washwashed with saturated aq. sodium bicarbonate (2×25 mL), 2.5 N aq. NaOH (25 mL), and saturated aq. brine (25 mL)
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. customdecanted
  5. customevaporated
  6. customThe crude product was purified by FC
  7. washeluting with 10% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-1623410797d74b95b16a7a64d25cef74
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06358979B1

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