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

HRID 1386768Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1386768
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

Komponenten

6

Edukt 3

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

Produkt 1

HCID 181877152-(2-(1-(Benzyloxycarbonyl)piperidin-4-yl)ethyl)-2-phenyl-1,3-dithiolaneAusbeute 92,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4574a55d742c4640b59651070545223f
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265434B1

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