1,1-Dimethylethyl 1-pyrrolidinecarboxylate

liquid

Racemic 2-benzyl pyrrolidine was synthesized using a modified literature procedure (the Sparteine chiral ligand was omitted), see: J. Am. Chem. Soc. 1994, 116, 3231 as follows: A) Procedure for the preparation of Boc-protected pyrrolidine To a stirred mixture of pyrrolidine (10.0 g, 0.14 mol) in DCM (150 mL) at 0°C was added TEA (15.6 g, 0.15 mol) followed by (Boc)20 (30.6 g, 0.14 mol) and the mixture was stirred at RT for 1 h, TLC showed that pyrrolidine had disappeared. The mixture was washed with a 1 M aqueous HC1 solution (100 mL), brine, dried over Na2S04, filtered and concentrated in vacuo to give the product (24.0 g, 100percent) as a colorless oil, which was used in the next step directly.General procedure: To (Boc)General procedure: An amine (1 mmol) was added to a magnetically stirred mixture of SBA-15-Ph-SO3H (1 mol percent, 4 mg) and (Boc)2O (1.1 mmol) at room temperature. The progressof the reaction was monitored by thin-layer chromatography (TLC). After completion of the reaction, the reaction mixture was diluted with EtOH (5 mL)and centrifuged. Then the clear liquid was separated, and the residue containing the catalyst was kept for recovery. EtOH was distilled off under vacuum to yield the highly pure N-Boc derivative.General procedure: Amine (1 mmol) and di-tert-butyl dicarbonate [(Boc)2O] (1.1 mmol) were placed in a microwave reaction vial. The LG microwave oven MG 555f was programmed to 300 W at 100 °C. The reaction was monitored using TLC. After the reaction, ice water was added to the reaction mixture which resulted in the precipitation of the product. The solid product was merely filtered off and washed with excess cold water. The product was pure enough for all practical purposes. For characterization purpose, it was further purified by column chromatography (Neutral Alumina as adsorbent, solvent system: Hexane: Ethyl acetate (7.5:2.5)).#10;Synthesis of N-BOC pyrrolidine: In a reaction flask, pyrrolidine (11.3 mL, 133 mmol) and dichloromethane (120 mL) were added, and cooled to -10 to 0 ° C, followed by dropwise addition of BOC2O (24.6 g, 112 mmol) dissolved in 35 mL Dichloromethane solution. After the addition, the mixture was stirred at room temperature for 3-5 hours. The solvent was evaporated to dryness, and then evaporated to dryness to afforded 16.6 g of colorless oily liquid, yield: 87 percentThe tetrahydro-3aH-[1, 3] dioxolo [4, 5-c] pyrrole hydrochloride was made as follows: A mixture of 3-pyrroline (2, 5-DIHYDRO-LH-PYRROLE) (25g; 0.36mole ; 65percent pure containing pyrrolidine) and ethyl acetate (125mL) was cooled to 0°C and a solution of BOC2O (78.95g ; 0. 36MOL) in ethyl acetate (125mL) was added dropwise while keeping the temperature between 5 and 10°C. The reaction mixture was then left to rise to ambient temperature overnight. The organic phase was washed successively with water, HC1 0. 1N, water, saturated sodium hydrogen carbonate, brine and dried over magnesium sulphate. Filtration and evaporation of the solvent gave a colourless oil (62g) containing 37percent of pyrrolidine-Boc in addition to the desired tert-butyl 2, 5-dihydro-lH-pyrrole-l- carboxylate (62g, 100percent based on conversion of both pyrroline and pyrrolidine). IH NE SPECTRUM : (CDC13) 1.45 (s, 9H), 4.1 (d, 4H), 6.75 (M, 2H) Pyrrolidone-Boc: 1.50 (s, 9H), 1.80 (br s, 4H), 3.3 (br s, 4H)

N-Boc-pyrrolidine is a boc-protected cyclic amine used as a building block in the preparation of diastereomers by usually undergoing α'-lithiations and electrophilic substitution reactions.

Molecular Weight:171.24
XLogP3:1.6
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:171.125928785
Monoisotopic Mass:171.125928785
Topological Polar Surface Area:29.5
Heavy Atom Count:12
Complexity:166
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes