(S)-1-Boc-pyrrolidine-3-carboxylic acid methyl ester synthesis
- Product Name:(S)-1-Boc-pyrrolidine-3-carboxylic acid methyl ester
- CAS Number:313706-15-9
- Molecular formula:C11H19NO4
- Molecular Weight:229.27
140148-70-5
74-88-4
313706-15-9
To a solution of (S)-1-BOC-pyrrolidine-3-carboxylic acid (863 mg, 4.01 mmol) and K2CO3 (829 mg, 6.00 mmol) in anhydrous DMF (8 mL) was added iodomethane (300 μL, 4.82 mmol). The reaction mixture was stirred at room temperature for 4 hours. After completion of the reaction, water was added and extracted three times with ether (Et2O). The organic phases were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by fast column chromatography (eluent: n-hexane/ethyl acetate = 3:1) to afford the target product (S)-1-Boc-3-carboxypyrrolidinium methyl ester (916 mg, 100%) as a colorless oil. The product was confirmed by 1H NMR (400 MHz, CDCl3): δ 3.70 (3H, s), 3.65-3.28 (4H, m), 3.10-2.98 (1H, m), 2.18-2.05 (2H, m), 1.45 (9H, s). lRMS (ESI, [M + Na]+) showed the molecular ion peak as 252.1.
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Yield: 100%
Reaction Conditions:
with potassium carbonate in N,N-dimethyl-formamide at 20; for 4 h;
Steps:
3.1.9. Compound 7
To a solution of 615 (863 mg, 4.01 mmol), K2CO3 (829 mg, 6.00 mmol) in dry DMF (8 mL) was added MeI (300 μL, 4.82 mmol). The mixture was stirred at rt for 4 h, water was added and the whole was extracted with Et2O (three times). The Et2O solution was dried over MgSO4 and evaporated, and the residue was flash-chromatographed (n-hexane/AcOEt=3:1) to give 7 (916 mg, 100%) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 3.70 (3H, s), 3.65-3.28 (4H, m), 3.10-2.98 (1H, m), 2.18-2.05 (2H, m), 1.45 (9H, s). LRMS (ESI, [M+Na]+) 252.1.
References:
Otani, Yuko;Hori, Tetsuharu;Kawahata, Masatoshi;Yamaguchi, Kentaro;Ohwada, Tomohiko [Tetrahedron,2012,vol. 68,# 23,p. 4418 - 4428] Location in patent:experimental part
67-56-1
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122684-33-7
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313706-15-9
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313706-15-9
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313706-15-9
95 suppliers
$22.00/100mg
72925-16-7
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140148-70-5
200 suppliers
$8.00/100mg