Piperidine → 4-hydroxy-2-phenethyl-2-phenyl-5-(2-sec-butylphenyl)sulfanyl-3H-pyran-6-one

HRID 481891Notes

Reaction equation

HRID 481891 reaction equation
Br[C:2]1[C:3](=[O:23])[O:4][C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][C:7]=1[OH:8].[CH:24]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[SH:34])([CH2:26][CH3:27])[CH3:25].N1CCCCC1>ClCCl>[CH:24]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34][C:2]1[C:3](=[O:23])[O:4][C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][C:7]=1[OH:8])([CH2:26][CH3:27])[CH3:25]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 2407042-Sec-butylbenzenethiolHCID 547216393-bromo-5,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

Product 1

HCID 546890154-hydroxy-2-phenethyl-2-phenyl-5-(2-sec-butylphenyl)sulfanyl-3H-pyran-6-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared as described in General Method 6 from 2.0 mmol of 3-bromo-5,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one (prepared in example BBB), 2.1 mmol of 2-sec-butylbenzenethiol, and 2.1 mmol of piperidine in 25 mL of dichloromethane. The product was chromatographed on silica gel, eluting first with chloroform and then with 5% methanol in chloroform, to give the title compound (m.p. 67°-68° C.). 1H NMR (DMSO-d6) δ0.82 (q, 3H), 1.09 (t, 3H), 1.46-1.61 (m, 2H), 2.26 (m, 2H), 2.35 (m, 1H), 2.62 (m, 1H), 2.98 (m, 1H), 3.47 (q, 2H), 5.90 (t, 1H), 6.56 (t, 1H), 6.94 (t, 1H), 7.07-7.18 (m, 4H), 7.25 (m, 2H), 7.45 (m, 5H).

Workup

  1. customThe title compound was prepared
  2. customThe product was chromatographed on silica gel
  3. washeluting first with chloroform

Sources & evidence

ORD record
ord-8ff6367c2bd0489988d8c5c97bd9b1c4
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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