3-(Chloromethyl)pyridine hydrochloride → HCID 54279304, compound

HRID 555751Notes

Reaction equation

HRID 555751 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:14][CH2:13][C@@H:12]([OH:15])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Cl.Cl[CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1>C1COCC1>[C:3]([O:7][C:8]([N:10]1[CH2:14][CH2:13][C@@H:12]([O:15][CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 24758Sodium hydrideHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 54279304HCID 54279304, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

55% of NaH in mineral oil (160 mg, 6.68 mmol) is added to a solution of (R)-3-Hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (500 mg, 2.67 mmol) in THF (8 mL) at 0° C. After 15 min, 3-chloromethyl-pyridine HCl salt (526 mg, 3.20 mmol) is added, and the reaction mixture is stirred at 40° C. After completion, the reaction mixture is quenched by H2O, EtOAc is added and the organic layer is washed with brine, dried over MgSO4 and evaporated in vacuo. Silica gel flash chromatography of the residue affords the title compound as a white powder; ES-MS: M+=279.2: AtRet=2.80.

Workup

  1. customAfter completion, the reaction mixture is quenched by H2O, EtOAc
  2. additionis added
  3. washthe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-70092af1a3504547bc44360fefcde6ba
Source dataset
uspto-grants-2011_11
Patent number
US08053457B2

Reaction notes

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