| Identification | Back Directory | [Name]
1-Pyrrolidinecarboxylic acid, 3-ethynyl-, 1,1-dimethylethyl ester | [CAS]
287193-00-4 | [Synonyms]
287193-00-4
1-Boc-3-ethynylpyrrolidine
1-Boc-3-ethynylpyrrolidin...
tert-Butyl 3-ethynyl-1-pyrrolidinecarboxylate
tert-butyl 3-ethynylpyrrolidine-1-carboxylate
1-Pyrrolidinecarboxylic acid, 3-ethynyl-,1,1-dimethyl ester
3-ethynyl-1-Pyrrolidinecarboxylic acid 1,1-dimethylethyl ester
1-Pyrrolidinecarboxylic acid, 3-ethynyl-, 1,1-dimethylethyl ester | [Molecular Formula]
C11H17NO2 | [MDL Number]
MFCD10698160 | [MOL File]
287193-00-4.mol | [Molecular Weight]
195.26 |
| Chemical Properties | Back Directory | [Boiling point ]
249.2±29.0 °C(Predicted) | [density ]
1.04±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [form ]
solid | [pka]
-2.53±0.40(Predicted) | [Appearance]
White to off-white Solid | [Optical Rotation]
0.9898°(C=0.1566g/100ml MEOH) | [InChI]
1S/C11H17NO2/c1-5-9-6-7-12(8-9)10(13)14-11(2,3)4/h1,9H,6-8H2,2-4H3 | [InChIKey]
KTDGOUSDBBFBRO-UHFFFAOYSA-N | [SMILES]
CC(C)(OC(N1CCC(C#C)C1)=O)C |
| Hazard Information | Back Directory | [Application]
tert-butyl 3-ethynylpyrrolidine-1-carboxylate is a useful research chemical. | [Synthesis]
GENERAL STEPS: 1-Boc-3-pyrrolidinecarboxaldehyde (580 mg, 2.91 mmol) was dissolved in methanol (15 mL) at room temperature, and potassium carbonate (1.00 g, 7.28 mmol) and dimethyl (1-diazido-2-oxopropyl)phosphonate (839 mg, 4.37 mmol) were added sequentially. The reaction mixture was stirred at room temperature for 3 h. After completion of the reaction, it was filtered through a short diatomaceous earth pad and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography with an eluent gradient of 0 to 50% ethyl acetate/hexane to give a colorless oily product. The product was allowed to stand in a refrigerator and cured to give 1-Boc-3-ynylpyrrolidine white solid (374 mg, 66% yield). | [References]
[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 18, p. 8417 - 8443
[2] Patent: US2016/9720, 2016, A1. Location in patent: Paragraph 0250
[3] Patent: US2016/9711, 2016, A1. Location in patent: Paragraph 0242; 0243; 0244 |
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