1-Pyrrolidinecarboxylic acid, 2-(hydroxyMethyl)-4,4-diMethyl-, 1,1-diMethylethyl ester, (2R)- synthesis

5synthesis methods

Product Name:1-Pyrrolidinecarboxylic acid, 2-(hydroxyMethyl)-4,4-diMethyl-, 1,1-diMethylethyl ester, (2R)-
CAS Number:1417743-45-3
Molecular formula:C12H23NO3
Molecular Weight:229.32

(R)-5-(hydroxymethyl)-3,3-dimethylpyrrolidin-2-one

493035-98-6
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1-Pyrrolidinecarboxylic acid, 2-(hydroxyMethyl)-4,4-diMethyl-, 1,1-diMethylethyl ester, (2R)-

1417743-45-3
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Yield:1417743-45-3 435 mg

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 20; for 28.5 h;Inert atmosphere;Reflux;

Steps:

37 Description 37: (H)-feri-butyl 2-(hydroxymethyl)-4,4-dimethylpyrrolidine-1- carboxylate (D37)

To an ice cooled suspension of LiAIH₄ (219 mg, 5.78 mmol) in THF (10 ml) under N₂, a solution of (f?)-5-(hydroxymethyl)-3,3-dimethylpyrrolidin-2-one (D36) (690 mg, 4.82 mmol) in THF (10 ml) was added dropwise. The reaction was allowed to warm to RT over 30 min then refluxed for 5 hrs. LiAIH₄ (219 mg, 5.78 mmol) was added to the mixture and the reaction stirred for 18 hrs then a further addition of LiAIH₄ (219 mg, 5.78 mmol) was done and the reaction refluxed for additional 5 hrs. The reaction mixture was cooled to 0°C prior sequentially addition of water (0.87 ml), 15% NaOH (0.87 ml) and water (2.58 ml). The resulting slurry solution was filtered off; the filtrated was diluted with water (10 ml) and basified to pH~12 with Na₂CO₃ before adding dropwise a solution of Boc₂O (1 .37 g, 6.26 mmol) in THF (10 ml). The resulting mixture was stirred for 24 hrs then extracted with EtOAc (3x30ml). The organic phases were washed with NaCI sat., dried onto Na₂SO₄ and evaporated in vacuo to afford the title compound (D37) (435 mg). MS: (ES/+) m/z: 252.2 [MH+Na⁺] C12H23NO3 requires 229.17 ¹ H NMR (400MHz, CHCI3-d) δ (ppm): 5.25 - 5.09 (m, 1 H), 4.13 - 3.99 (m, 1 H), 3.62 (d, J = 7.9 Hz, 2 H), 3.39 - 3.23 (m, 1 H), 3.08 - 2.92 (m, 1 H), 1 .87 - 1 .73 (m, 1 H), 1 .49 (s, 9 H), 1 .38 - 1 .25 (m, 1 H), 1 .09 (s, 3 H), 1 .03 (s, 3 H)