Hydrochloric Acid → ((S)-1-piperidin-4-yl-pyrrolidin-2-yl)-methanol dihydrochloride

HRID 1692381Notes

Reaction equation

HRID 1692381 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][CH2:16][C@H:15]2[CH2:19][OH:20])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:21]>CCO.O1CCOCC1>[ClH:21].[ClH:21].[NH:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH2:18][CH2:17][CH2:16][C@H:15]2[CH2:19][OH:20])[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 574411334-((S)-2-Hydroxymethyl-pyrrolidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester2×

Product 1

HCID 66901571((S)-1-piperidin-4-yl-pyrrolidin-2-yl)-methanol dihydrochlorideYield 82%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 3.00 g (10.5 mmol) of 4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (intermediate 3A) in 70 ml of EtOH was treated at RT with 5.27 ml (21.1 mmol) of hydrochloric acid in 1,4-dioxane (4 molar) and the mixture was heated up to 100° C. After two hours, the solvents were evaporated and the residue was re-crystallized from MeOH/MeCN and Et2O to give 2.21 g (82%) of the title compound as colorless solid. MS: 185.2 (MH+).

Workup

  1. customthe solvents were evaporated
  2. customthe residue was re-crystallized from MeOH/MeCN and Et2O

Sources & evidence

ORD record
ord-f0d9b5ea65b542568c0bd3f50635657f
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Reaction notes

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