ChemicalBook CAS DataBase List (S)-1-Boc-pyrrolidine-3-carboxylic acid methyl ester

(S)-1-Boc-pyrrolidine-3-carboxylic acid methyl ester synthesis

5synthesis methods

Product Name:(S)-1-Boc-pyrrolidine-3-carboxylic acid methyl ester
CAS Number:313706-15-9
Molecular formula:C11H19NO4
Molecular Weight:229.27

(3S)-1-(tert-Butoxycarbonyl)-3-pyrrolidinecarboxylic acid

140148-70-5

74-88-4

(S)-1-Boc-pyrrolidine-3-carboxylic acid methyl ester

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.

140148-70-5
202 suppliers
$8.00/100mg

74-88-4
357 suppliers
$15.00/10g

313706-15-9
94 suppliers
$22.00/100mg

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 Synthesis