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

HRID 751645Notes

Reaction equation

HRID 751645 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+].[CH3:16]I>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][CH3:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 12050278(S)-tert-Butyl 3-methoxypyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-3-Hydroxypyrrolidine-1-carboxylic acid tert-butyl ester (Omega Chemical Company) (950 mg, 5.55 mmol) was methylated and purified in a similar way to Preparation 67 using 60% sodium hydride dispersion (260 mg, 6.50 mmol) and methyl iodide (0.5 mL, 8.06 mmol) in DMF (15 ml). 1H NMR and Rf were identical to the (R)-enantiomer.

Sources & evidence

ORD record
ord-4e43c030820340d792529bc2520ebfcb
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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