Methanol → HCID 9856229, compound

HRID 983691Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:15])[CH2:4][C@:5]1([CH2:11][N:12]=[C:13]=[O:14])[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6]1.C1(C)C=CC=CC=1.[CH3:23][OH:24]>>[CH3:1][O:2][C:3](=[O:15])[CH2:4][C@:5]1([CH2:11][NH:12][C:13]([O:24][CH3:23])=[O:14])[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6]1

Participants

Reactant 3

HCID 887Methanol

HCID 1140Toluene

HCID 58626984HCID 58626984, compound

Product 1

HCID 9856229HCID 9856229, compoundYield 77%

Procedure

((1S,3R)-1-Isocyanatomethyl-3-methyl-cyclopentyl)-acetic acid methyl ester (5.19 g, 24.5 mmol) was refluxed in methanol (30 mL) and toluene (80 mL) for 17 hours and then allowed to cool to room temperature. The solvent was removed under reduced pressure, and the residue was purified by chromatography (silica gel, heptane-ethyl acetate 9:1) to give 4.62 g (77%) of [(1S,3R)-1-(methoxycarbonylamino-methyl)-3-methyl-cyclopentyl]-acetic acid methyl ester;

Workup

customThe solvent was removed under reduced pressure
customthe residue was purified by chromatography (silica gel, heptane-ethyl acetate 9:1)

Sources & evidence

ORD record: ord-fe38faab83f14e7fb450df2adb764b1f
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06864390B2

Reaction notes

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