3-(5-Chloro-pyrimidin-4-yl)-3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester → 3-(5-Chloro-pyrimidin-4-yl)-8-aza-bicyclo{3.2.1]octan-3-ol hydrochloride

HRID 2202789Notes

Reaction equation

HRID 2202789 reaction equation
C(OC([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11]([C:17]1[C:22]([Cl:23])=[CH:21][N:20]=[CH:19][N:18]=1)([OH:16])[CH2:12]2)=O)(C)(C)C>Cl.O1CCOCC1>[ClH:23].[Cl:23][C:22]1[C:17]([C:11]2([OH:16])[CH2:12][CH:13]3[NH:8][CH:9]([CH2:15][CH2:14]3)[CH2:10]2)=[N:18][CH:19]=[N:20][CH:21]=1

Participants

4

Reactant 1

HCID 674659213-(5-Chloro-pyrimidin-4-yl)-3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

Product 1

HCID 866848213-(5-Chloro-pyrimidin-4-yl)-8-aza-bicyclo{3.2.1]octan-3-ol hydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

3-(5-Chloro-pyrimidin-4-yl)-3-hydroxy-8-aza-bicyclo{3.2.1]octane-8-carboxylic acid tert-butyl ester (0.14 g, 0.41 mmol) was dissolved in a solution of hydrogen chloride in dioxane (4 N, 2 mL). The mixture was stirred for 1 hour and the solvent removed by evaporation under vacuum to afford the title compound. LCMS m/z 240.3 [M+H]+. R.T.=0.36 min (Analytical Method 3).

Workup

  1. customthe solvent removed by evaporation under vacuum

Sources & evidence

ORD record
ord-ef5bca1cc02443f7a4def4b36c634505
Source dataset
uspto-grants-2016_06
Patent number
US09365564B2

Reaction notes

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