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

HRID 2303629Notes

Reaction equation

HRID 2303629 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-978f92e6f2794a839f9935d20ab1560f
Source dataset
uspto-grants-2002_08
Patent number
US06432981B1

Reaction notes

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