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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1867366Generated: October 29, 2026

Methyl iodide → HCID 68432352, compound

https://huagongshe.com/reaction/1867366

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantSodium hydrideHCID 24758—
ReactantPotassium bisulfateHCID 516920—
ReactantTert-butyl 3-(hydroxymethyl)-3-methylpiperidine-1-carboxylateHCID 22258928—
SolventDimethylformamideHCID 6228—
ProductHCID 68432352HCID 6843235264.2%

Reaction Steps

A solution of 0.37 g (1.60 mmol) of (rac)-3-hydroxymethyl-3-methyl-piperidine-1-carboxylic acid tert-butyl ester (intermediate 30B) and 0.20 ml (3.20 mmol) of iodomethane in 15 ml of DMF was treated at 0° C. with 0.08 g (1.92 mmol) of NaH (55% in oil). The reaction was stirred for 2 h at 0° C., neutralized with cold aqueous 10% KHSO4 and extracted with Et2O (3×). The organic phases were washed with aqueous saturated NaHCO3, aqueous 10% NaCl, dried over Na2SO4 evaporated and purified by flash silica gel column (n-heptane/EtOAc 95:5) to yield 0.25 g (64%) of the title compound as colorless liquid. MS: 244.1 (MH+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07632829B2
Source datasetuspto-grants-2009_12
ORD IDord-4eabf206894a443792c417e0d64a2f74
Source noteuspto-grants-2009_12