Methanol → HCID 58626992, compound

HRID 983685Notes

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 9920758HCID 9920758, compound

Product 1

HCID 58626992HCID 58626992, compoundYield 29%

Procedure

((1R,3R)-1-Isocyanatomethyl-3-methyl-cyclopentyl)-acetic acid methyl ester (7.82 g, 37 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 to heptane:ether 8:2) to give 2.60 g (29%) of [(1R,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 to heptane:ether 8:2)

Sources & evidence

ORD record: ord-f17d209fea114d8d843bdb34c000a5ee
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06864390B2

Reaction notes

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