Hydrochloric Acid → 4-(7-Propyl-isoquinolin-6-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 404744Notes

Reaction equation

HRID 404744 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([S:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][C:24]=2Cl)[CH:21]=[N:20][CH:19]=[CH:18]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1C(=O)[CH2:30][CH2:29][CH2:28]1.C([Mg]Cl)CC.Cl>C1COCC1.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[Fe].C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([S:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][C:24]=2[CH2:28][CH2:29][CH3:30])[CH:21]=[N:20][CH:19]=[CH:18]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 592908234-(7-Chloro-isoquinolin-6-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl esterHCID 178455855HCID 178455855, compound

Product 1

HCID 592906304-(7-Propyl-isoquinolin-6-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 11110968Iron (III) acetylacetonateCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 200 mg (0.52 mmol) 4-(7-Chloro-isoquinolin-6-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester (274) dissolved in 5 ml THF and 1 ml NMP were added 20 mg (0.055 mmol) Ferric (III) acetylacetonate. To the red solution 0.3 ml of propylmagnesium-chloride (2M in THF) were added and 2 min stirred at RT. 1 ml 1N HCl and 20 ml diethyl ether were added and the organic layer was washed with brine. The organic phases were dried over Sodium sulfate and evaporated. The residue was purified by HPLC. 85 mg of 4-(7-Propyl-isoquinolin-6-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester could be obtained as the trifluoroacetate.

Workup

  1. washthe organic layer was washed with brine
  2. dry with materialThe organic phases were dried over Sodium sulfate
  3. customevaporated
  4. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-d8b47be0070647619a4d67840443e4c8
Source dataset
uspto-grants-2014_06
Patent number
US08748614B2

Reaction notes

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