Piperidine → Methyl 2-[[5,6-dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-phenyl-2H-pyran-3-yl]thio]benzoate

HRID 481898Notes

Reaction equation

HRID 481898 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].[C:24]([O:33][CH3:34])(=[O:32])[C:25]1[C:26](=[CH:28][CH:29]=[CH:30][CH:31]=1)[SH:27].N1CCCCC1>ClCCl>[OH:8][C:7]1[CH2:6][C:5]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:4][C:3](=[O:23])[C:2]=1[S:27][C:26]1[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=1[C:24]([O:33][CH3:34])=[O:32]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 547216393-bromo-5,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

Product 1

HCID 54721613Methyl 2-[[5,6-dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-phenyl-2H-pyran-3-yl]thio]benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared as described in General Method 6 from 1.9 mmol of 3-bromo-5,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one (prepared in example BBB), 2.2 mmol of methyl thiosalicylate and 2.1 mmol of piperidine in 30 mL of dichloromethane. The crude product was chromatographed on silica gel, eluting first with chloroform and then with 5% methanol in chloroform, to give the title compound (m.p. 91°-92° C.). 1H NMR (DMSO-d6) δ2.25 (m, 2H), 2.38 (m, 1H), 2.62 (m, 1H), 3.44 (q, 2H), 3.82 (s, 3H), 6.06 (bd, 1H), 6.90 (t, 1H), 7.05-7.52 (m, 11H), 7.81 (dd, 1H).

Workup

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

Sources & evidence

ORD record
ord-24325126a05b4ed48da91536c6c02a8d
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

Loading…