Dichloromethane → dimethyl(2S,3S,5S)-5-tert-butoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

HRID 61478Notes

Reaction equation

HRID 61478 reaction equation
[C:1]([O:5][C@@H:6]1[CH2:11][NH:10][C@H:9]([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:8]([C:26]([O:28][CH3:29])=[O:27])[CH2:7]1)([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.Cl[C:34]([O:36][CH3:37])=[O:35]>CN(C)C1C=CN=CC=1>[C:1]([O:5][C@@H:6]1[CH2:11][N:10]([C:34]([O:36][CH3:37])=[O:35])[C@H:9]([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:8]([C:26]([O:28][CH3:29])=[O:27])[CH2:7]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6586Methyl chloroformateHCID 67304371Methyl (2s,3s,5s)-5-tert-butoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-3-carboxylate

Product 1

HCID 67304316dimethyl(2S,3S,5S)-5-tert-butoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a mixture of methyl(2S,3S,5S)-5-tert-butoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-3-carboxylate (0.03345 g, 8.290E-5 mol) and 4-dimethylaminopyridine (0.0152 g, 0.000124 mol) in methylene chloride (1.50 mL, 0.0234 mol) was added methyl chloroformate (0.00833 mL, 0.000108 mol). The reaction was stirred at rt overnight. After quenched with aq. sodium bicaronate, the reaction was extracted with ethyl acetate. The combined organic layers were washed with brine, dried, concentrated to dry. The resulting residue was used directly in next step. MS (ESI): (M+H)+=462.2.

Workup

  1. customAfter quenched with aq. sodium bicaronate
  2. extractionthe reaction was extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto dry

Sources & evidence

ORD record
ord-d4e3a1a9804049138007034ff1f6ec5a
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Reaction notes

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