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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 425802Generated: October 29, 2026

Diethyl Ether → [(1S,2S,5R)-2-aminomethyl-7-methyl-3-aza-bicyclo[3.3.0]oct-3-yl]-(2-methyl-5-m-tolyl-thiazol-4-yl)-methanone

https://huagongshe.com/reaction/425802

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
ReactantPotassium CarbonateHCID 11430—
Reactant2,2,2-trifluoro-N-[(1S,2S,5R)-3-(2-methyl-5-m-tolyl-thiazole-4-carbonyl)-7-methyl-3-aza-bicyclo[3.3.0]oct-2-ylmethyl]-acetamideHCID 86643545—
SolventMethanolHCID 887—
Product[(1S,2S,5R)-2-aminomethyl-7-methyl-3-aza-bicyclo[3.3.0]oct-3-yl]-(2-methyl-5-m-tolyl-thiazol-4-yl)-methanoneHCID 59411601—

Reaction Steps

2,2,2-trifluoro-N-[(1S,2S,5R)-3-(2-methyl-5-m-tolyl-thiazole-4-carbonyl)-7-methyl-3-aza-bicyclo[3.3.0]oct-2-ylmethyl]-acetamide (1.96 g) was dissolved in MeOH (20 mL) and a sat. aq. K2CO3 solution was added (20 mL). The reaction mixture was stirred overnight at RT. Ether was added to the reaction mixture and the org. layer was extracted with aq. HCl (25%) and aq. HCl (1M). The org. phase was discarded and the aq. layers were basified with aq. 30% NaOH and then extracted with DCM. The combined org. extracts were washed with a sat. aq. NaHCO3 solution, dried over anh. MgSO4, filtered and concentrated to yield the title compound as a light orange oil which was used without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08106215B2
Source datasetuspto-grants-2012_01
ORD IDord-411e7770552146b6a202d07c7912e894
Source noteuspto-grants-2012_01