Hydrochloric Acid → (R)-1-(6-Amino-pyridin-3-ylmethyl)-pyrrolidin-3-ol

HRID 43131Notes

Reaction equation

HRID 43131 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]2[CH2:19][CH2:18][C@@H:17]([OH:20])[CH2:16]2)=[CH:10][N:9]=1)(C)(C)C.Cl.CO>O1CCOCC1>[NH2:7][C:8]1[N:9]=[CH:10][C:11]([CH2:14][N:15]2[CH2:19][CH2:18][C@@H:17]([OH:20])[CH2:16]2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 66914597[5-((R)-3-hydroxy-pyrrolidin-1-ylmethyl)-pyridin-2-yl]carbamic acid tert-butyl ester

Product 1

HCID 66914544(R)-1-(6-Amino-pyridin-3-ylmethyl)-pyrrolidin-3-olYield 89.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of [5-((R)-3-hydroxy-pyrrolidin-1-ylmethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester (Step 100.2) (210 mg, 0.72 mmol), a 4 N solution of HCl in dioxane (2 mL), and MeOH (2 mL) was stirred for 16 h at rt and concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 89:10:1) to afford 125 mg of the title compound as a yellow oil. Title compound: ESI-MS: 194.1 [M+H]+; TLC: Rf=0.05 (DCM/MeOH, 9:1).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 89:10:1)

Sources & evidence

ORD record
ord-258974b4108548f59e55ef99e91fd56c
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

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