HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Ethyl (+/-)-[2-(3',4'-dihydro-2'-hydroxyspiro-[cyclopentane-1,1'(2'H)-napthalen]-2'-yl)ethyl]-carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | (+/-)-2'-(2-Aminoethyl)-3',4'-dihydrospiro[cyclopentane-1,1'(2'H)-napthalen]-2'-ol | HCID 19983233 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Ethyl (+/-)-[2-(3',4'-dihydro-2'-hydroxyspiro-[cyclopentane-1,1'(2'H)-napthalen]-2'-yl)ethyl]-carbamate | HCID 86745264 | 98% |
Reaction Steps
A solution of the product from Example 9 (1.05 g, 4.28 mmol) and triethylamine (0.44 g, 4.35 mmol) in 10 mL of CH2Cl2 was cooled to 0° C. and ethyl chloroformate (0.47 g, 4.33 mmol) in 5 mL CH2Cl2 was added dropwise. The reaction was warmed to room temperature and washed with water. The aqueous phase was extracted with CH2Cl2 (3×20 mL) and the combined organic extracts were dried (MgSO4), filtered and concentrated. The residue was purified by chromatography (silica gel, 1:1 heptane/ethyl acetate) to give the title compound (1.33 g, 98%) as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05070093 |
| Source dataset | uspto-grants-1991_12 |
| ORD ID | ord-0edee85f3a33489abf2d2811f9d81dc3 |
| Source note | uspto-grants-1991_12 |