HCID 68536173, compound → HCID 53318069, compound

HRID 1172273Notes

Reaction equation

HRID 1172273 reaction equation
ClC(Cl)(Cl)CC([O:6][C:7]([CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([CH2:18][O:19][C:20]([C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[NH:24][CH:23]=2)=[O:21])[CH2:14][CH2:13]1)=[O:8])C>C1COCC1.OP([O-])(O)=O.[K+].[Zn]>[C:7]([CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([CH2:18][O:19][C:20]([C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[NH:24][CH:23]=2)=[O:21])[CH2:14][CH2:13]1)([OH:8])=[O:6]

Participants

5

Reactant 1

HCID 68536173HCID 68536173, compound

Product 1

HCID 53318069HCID 53318069, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolventHCID 516951Monobasic potassium phosphateSolvent

Procedure

1H-indole-3-carboxylic acid 1-[3-(2,2,2-trichloroethyl-ethoxycarbonyl)-propyl]piperidine-4-ylmethyl ester (0.48 g, 1.0 mmol) was dissolved in a mixture of THF (25 ml) and aqueous 1 M KH2PO4 (5 ml). Zn-powder (0.66 g, 10.0 mmol) was added and the resulting mixture stirred at room temperature for 24 h. The reaction mixture was filtered through a pad of kiselguhr and the filtrate evaporated in vacuo. The residue was separated with flash chromatography (SiO2, EtOAc/MeOH (2:1)). The expected product was obtained as a white solid (0.29 g, 84.2%). Conversion to the hydrochloride salt was effected using etheral HCl.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of kiselguhr
  2. customthe filtrate evaporated in vacuo
  3. customThe residue was separated with flash chromatography (SiO2, EtOAc/MeOH (2:1))

Sources & evidence

ORD record
ord-65dcd85870de4622bdfc933771fa6106
Source dataset
uspto-grants-2010_11
Patent number
US07834010B2

Reaction notes

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