Methyl iodide → (R)-tert-Butyl 3-methoxypyrrolidine-1-carboxylate

HRID 1693389Notes

Reaction equation

HRID 1693389 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].CI.[C:18](OCC)(=O)C.CCCCCC>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][CH3:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylateHCID 21226206Ethyl acetate hexane

Product 1

HCID 34179484(R)-tert-Butyl 3-methoxypyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-3-Hydroxypyrrolidine-1-carboxylic acid tert-butyl ester (Sigma-Aldrich) (1.04 g, 5.55 mmol) was methylated and purified in a similar way to Preparation 67 using 60% sodium hydride dispersion (267 mg, 6.68 mmol) and methyl iodide (0.5 mL, 8.06 mmol) in DMF (15 ml). δH (CDCl3): 1.50 (9H, s), 1.94-2.02 (2H, m), 3.37 (3H, s), 3.38-3.58 (4H, m), 3.95 (1H, m); Rf 0.47 (ethyl acetate/hexane: 1/1).

Sources & evidence

ORD record
ord-a927e90ade9f436b812cb4e335c2f475
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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