Methyl iodide → N-benzyl-3-methoxypyrrolidine

HRID 1109728Notes

Reaction equation

HRID 1109728 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:16]I>C1COCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][CH3:16])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69889N-benzyl-3-pyrrolidinol

Product 1

HCID 19019527N-benzyl-3-methoxypyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2.0 g (11 3 mmoles) of N-benzyl-3-hydroxypyrrolidine in 10 ml of dry THF was added dropwise at room temperature to a stirred slurry of 0.53 g (12.4 mmoles) of 56% NaH in 10 ml of dry THF, under nitrogen atmosphere. After 2 h the solution was cooled to 0° C. and 1.8 g (12.4 mmoles) of methyl iodide were added.

Sources & evidence

ORD record
ord-836d2f4307b84e34875640e5f705b258
Source dataset
uspto-grants-1994_06
Patent number
US05322848

Reaction notes

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