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

HRID 1386768노트

반응식

HRID 1386768 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 (BF3.2CH3CO2H, 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-phenylpropyl)piperidine (930 mg, 2.65 mmol) in CH2Cl2 (4.0 mL) at RT. After 6 h, the mixture was diluted with ether (50 mL) and washed with saturated aq. NaHCO3 (2×25 mL), 2.5 N NaOH (25 mL), and saturated aq. NaCl (25 mL). The organic layer was dried (Na2SO4), decanted, and evaporated. The crude product was purified by flash column chromatography on silica gel eluting with 9:1 v/v hexanes/EtOAc to give 1.05 g of the title compound as a colorless liquid: 1H NMR (400 MHz) S 7.66 (d, J=8, 2H), 7.38-7.26 (m, 7H), 7.22 (t, J=8), 1H), 5.10 (s, 2H), 4.18-4.02 (m, 2H), 3.41-3.32 (m, 2H), 3.29-3.20 (m, 2H), 2.79-2.62 (m, 2H), 2.40-2.32 (m, 2H), 1.65-1.54 (m, 2H), 1.40-1.27 (m, 1H), 1.24-1.16 (m, 2H), 1.10-0.97 (m, 2H); ESI-MS 428 (M+H); HPLC A: 4.21 min.

후처리

  1. customat RT
  2. washwashed with saturated aq. NaHCO3 (2×25 mL), 2.5 N NaOH (25 mL), and saturated aq. NaCl (25 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customdecanted
  5. customevaporated
  6. customThe crude product was purified by flash column chromatography on silica gel eluting with 9:1 v/v hexanes/EtOAc

출처 및 근거

ORD 기록
ord-4574a55d742c4640b59651070545223f
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06265434B1

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