Hydrochloric Acid → 2-cyclopentyl N-piperidin-3-yl-L-leucinate dihydrochloride

HRID 632561Notes

Reaction equation

HRID 632561 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C@H:15]([C:20]([O:22][CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:9]1)=O)(C)(C)C.[ClH:28]>ClCCl.O1CCOCC1>[ClH:28].[ClH:28].[NH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C@H:15]([C:20]([O:22][CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27]2)=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 866864133-((S)-1-cyclopentyloxycarbonyl-3-methyl-butylamino)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866864142-cyclopentyl N-piperidin-3-yl-L-leucinate dihydrochlorideYield 24%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-((S)-1-cyclopentyloxycarbonyl-3-methyl-butylamino)-piperidine-1-carboxylic acid tert-butyl ester (0.840 g, 2.20 mmol) in dichloromethane (5 mL) was added 4M hydrogen chloride in dioxane (10 mL). The reaction was stirred at room temperature for 90 minutes and then concentrated to give the product (184 mg, 24% yield). LC/MS: m/z 283 [M+H]+

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-65dbc7940e7b4010826560512f4aa94a
Source dataset
uspto-grants-2016_04
Patent number
US09321718B2

Reaction notes

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