(R)-tert-butyl 3-((S)-1-(3-chlorophenyl)-1,5-dimethoxypentyl)piperidine-1-carboxylate → (R)-3-((S)-1-(3-chlorophenyl)-1,5-dimethoxypentyl)-piperidine

HRID 2355420Notes

Reaction equation

HRID 2355420 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@:8]([C@@H:17]2[CH2:22][CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]2)([O:15][CH3:16])[CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[CH:5]=[CH:6][CH:7]=1>CC#N.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C@:8]([C@@H:17]2[CH2:22][CH2:21][CH2:20][NH:19][CH2:18]2)([O:15][CH3:16])[CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 67192256(R)-tert-butyl 3-((S)-1-(3-chlorophenyl)-1,5-dimethoxypentyl)piperidine-1-carboxylate

Product 1

HCID 59382902(R)-3-((S)-1-(3-chlorophenyl)-1,5-dimethoxypentyl)-piperidine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent

Procedure

A quarter of the (R)-tert-butyl 3-((S)-1-(3-chlorophenyl)-1,5-dimethoxypentyl)piperidine-1-carboxylate obtained in Step 1 (ca. 75 mg, ca. 0.1 mmol) was dissolved in CH3CN (30 mL) and 2 N HCl (25 mL). The mixture was vigorously stirred at rt for 2 d. The solvents were removed in vacuo to give the HCl salt of (R)-3-((S)-1-(3-chlorophenyl)-1,5-dimethoxypentyl)-piperidine, which was used without further purification. LC-MS (3 min) tR=1.22 min, m/z 328, 326 (M+H+).

Workup

  1. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-45cdca6040c2483080195a5eb26860ce
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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