1-Pyrrolidinecarboxylic acid, 2-(hydroxymethyl)-4-methyl-, 1,1-dimethylethyl ester, (2S,4S)- synthesis

9synthesis methods

Product Name:1-Pyrrolidinecarboxylic acid, 2-(hydroxymethyl)-4-methyl-, 1,1-dimethylethyl ester, (2S,4S)-
CAS Number:540501-56-2
Molecular formula:C11H21NO3
Molecular Weight:215.29

364750-81-2 Synthesis

(2S,4S)-N-Boc-4-methylpyrrolidine-2-carboxylic acid

364750-81-2
118 suppliers
$38.00/100mg

1-Pyrrolidinecarboxylic acid, 2-(hydroxymethyl)-4-methyl-, 1,1-dimethylethyl ester, (2S,4S)-

540501-56-2
35 suppliers
$45.00/2.5mg

Yield: 100%

Reaction Conditions:

with diborane in tetrahydrofuran at 0 - 20; for 2 h;

Steps:

20.6 Step 6) the preparation of compound 20-7
To a solution of compound 20- 1 (1 .12 g. 4.88 mmol) in THF (10.0 mL) at 0 °C was added borane (7.3 mL, 1 M in THF). and the mixture was stirred at rt for 2 hrs. After the reaction was completed, the mixture was quenched with MeOH (4.0 mL). The solvent THF was removed in vacuo, and the residue was dissolved in DCM (50 mL). The solution was washed with water (20 mL x 3), dried over anhydrous Na₂S0₄ and concentrated in vacuo, and the residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) = 3/1 ) to give the title compound as colorless slurry (1.03 g. 100%). The compound was characterized by the following spectroscopic data: MS (ESI. pos.ion) mlz: 216.29 [M+H] ⁺; NMR (400 MHz. CDC1₃) δ (ppm): 4.02 (s, 1 H). 3.99-3.87 (m, 1 H), 3.75-3.68 (m. 1 H), 3.66 (dd, 1 H, J = 11.6 Hz, 2.0 Hz), 3.57 (dd, 1H, J = 1 1.6 Hz. 7.4 Hz), 2.76 (t, 1H, J = 10.5 Hz), 2.19-2.06 (m, 2H), 1.46 (s, 9H). 1.01 (d, 3H, J = 6.2 Hz).

References:

SUNSHINE LAKE PHARMA CO., LTD.;ZHANG, Yingjun;ZHANG, Jiancun;XIE, Hongming;REN, Qingyun;TAN, Yumei;LUO, Huichao WO2014/19344, 2014, A1 Location in patent:Paragraph 00497