Dichloromethane → Dimethyl (2s,3s,5r)-5-[(methylsulfonyl)oxy]-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

HRID 535076Notes

Reaction equation

HRID 535076 reaction equation
[OH:1][C@H:2]1[CH2:7][N:6]([C:8]([O:10][CH3:11])=[O:9])[C@H:5]([C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[O:13])[C@@H:4]([C:26]([O:28][CH3:29])=[O:27])[CH2:3]1.C(N(CC)CC)C.C(Cl)Cl.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>>[CH3:40][S:41]([O:1][C@H:2]1[CH2:7][N:6]([C:8]([O:10][CH3:11])=[O:9])[C@H:5]([C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[O:13])[C@@H:4]([C:26]([O:28][CH3:29])=[O:27])[CH2:3]1)(=[O:43])=[O:42]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67304460dimethyl(2S,3S,5R)-5-hydroxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

Product 1

HCID 87348459Dimethyl (2s,3s,5r)-5-[(methylsulfonyl)oxy]-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

Procedure

To a stirred solution of dimethyl (2S,3S,5R)-5-hydroxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate (1.00 g, 0.00247 mol) and triethylamine (0.412 mL, 0.00296 mol) in methylene chloride (20.00 mL, 0.3120 mol) was added methanesulfonyl chloride (0.210 mL, 0.00271 mol). The mixture was stirred at rt overnight. After quenched with MeOH, the mixture was evaporated to dry in vacuo and diluted with ethyl acetate. The organic layers were washed with water, brine and dried, concentrated to dry. The residue was purified on silica gel, eluting with 0 to 80% EtOAc in hexane, to generate the mesylate compound (0.98 g, 82%). MS (ESI): (M+H)+=484.1.

Workup

  1. customAfter quenched with MeOH
  2. customthe mixture was evaporated
  3. customto dry in vacuo
  4. additiondiluted with ethyl acetate
  5. washThe organic layers were washed with water, brine
  6. customdried
  7. concentrationconcentrated
  8. customto dry
  9. customThe residue was purified on silica gel
  10. washeluting with 0 to 80% EtOAc in hexane

Sources & evidence

ORD record
ord-7589ffdf1dfe4d1b95292c5b79bdb08d
Source dataset
uspto-grants-2014_10
Patent number
US08853243B2

Reaction notes

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