ChemicalBook CAS DataBase List 2-HYDROXYMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

2-HYDROXYMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER synthesis

12synthesis methods

Product Name:2-HYDROXYMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
CAS Number:170491-63-1
Molecular formula:C10H19NO3
Molecular Weight:201.26

24424-99-5

498-63-5

2-HYDROXYMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

170491-63-1

Step 1. Synthesis of tert-butyl 2-hydroxymethylpyrrolidine-1-carboxylate Pyrrolidine-2-methanol (0.300 g, 1.98 mmol) was dissolved in dichloromethane (5.0 mL) and di-tert-butyl dicarbonate (0.650 g, 1.98 mmol) was added. The reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, the residue was purified by post-processing using Isco Combi-Flash Companion column chromatography (eluent: dichloromethane solution in 0-10% methanol) to afford tert-butyl 2-hydroxymethylpyrrolidine-1-carboxylate (0.590 g, 98% yield). 1H NMR (CDCl3, 300 MHz) δ 4.78 (br d, 1H), 4.05-3.90 (br, 1H), 3.67-3.53 (m, 2H), 3.49-3.41 (m, 1H), 3.34-3.26 (m, 1H), 2.00 (dddd, 1H), 1.85-1.72 (m, 2H). 1.60-1.50 (m, 1H), 1.46 (s, 9H).

24424-99-5 Synthesis

24424-99-5
858 suppliers
$13.50/25G

498-63-5
152 suppliers
$34.00/5g

170491-63-1
164 suppliers
$8.00/250mg

Yield:170491-63-1 98%

Reaction Conditions:

in dichloromethane at 20; for 16 h;

Steps:

353.1 Step 1. Synthesis of tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate
Step 1.
Synthesis of tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate
A solution of 2-pyrrolidinemethanol (0.300 g, 1.98 mmol) in CH₂Cl₂ (5.0 mL) and di-tert-butyl dicarbonate (0.650 g, 1.98 mmol) were used to carry out the reaction.
After the reaction was stirred at room temperature for 16 h and work-up, the residue was purified by Isco Combi-Flash Companion column chromatography (0-10% MeOH in CH₂Cl₂) to give tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate (0.590 g, 98%).
¹H NMR (CDCl₃, 300 MHz) δ 4.78 (br d, 1H), 4.05-3.90 (br, 1H), 3.67-3.53 (m, 2H), 3.49-3.41 (m, 1H), 3.34-3.26 (m, 1H), 2.00 (dddd, 1H), 1.85-1.72 (m, 2H), 1.60-1.50 (m, 1H), 1.46 (s, 9H).

References:

National Health Research Institutes;Ueng, Shau-Hua;Yeh, Shiu-Hwa;Lin, Shu-Yu;Shih, Chuan US2017/253569, 2017, A1 Location in patent:Paragraph 0994-0995

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