Chemical N-Boc-3-pyrrolidinone Description
Chemical N-Boc-3-pyrrolidinone Basic Attributes
Molecular Formula ：C9H15NO3
Molecular Mass ：185.22
Exact Mass ：185.105194
PSA ：46.6 A^2
H-bond Acceptor ：3
H-bond Donor ：0
Chemical N-Boc-3-pyrrolidinone Characteristics
Appearance ：White to yellow to orange Low Melting Solid
Density ：1.133±0.06 g/cm3(Predicted)
Melting Point ：34-38 °C(lit.)
Bolling Point ：270.9±33.0 °C(Predicted)
Flash Point ：>230 °F
Refractive Index ：1.486
Solubility ：Insoluble in water.
Storage Condition ：Store at 0-5°C
Chemical N-Boc-3-pyrrolidinone Safety Information
HS Code ：29339900
UN No. ：NONH for all modes of transport
Risk Code ：22-37/38-41-36/37/38-20/21/22
Safety Instructions ：26-36/37/39-36
Dangerous Mark ：Xn,Xi
P Code ：P261-P280-P305 + P351 + P338
Hazard Statements ：H302-H315-H318-H335
Hazard Note ：Irritant
Chemical N-Boc-3-pyrrolidinone Product Usage
1-tert-butoxycarbonyl-3-pyrrolidone is a starting material and a useful intermediate in organic synthesis.
Chemical N-Boc-3-pyrrolidinone Production Methods
To a cold (-78° C.) solution of oxalyl chloride (2.8 mL, 32.4 mmol) in CH Part A: To a solution of oxalyl chloride (1.3 mL, 15 mmol) in 20 mL of dichloromethane at -60° C. was added methyl sulfoxide dropwise over period of 10 min. After stirring at -60° C., a solution of 1,1-dimethylethyl 3-hydroxypyrrolidine-1-carboxylate (1.87 g, 10 mmol) in 20 mL of dichloromethane was added over 20 min. Then, diisopropylethylamine (8.8 mL, 50 mmol) was added over 5 min. The resulting mixture was stirred at -60° C. for 25 min, and at room temperature for 30 min. The reaction was diluted with dichloromethane (100 mL). The organic layer was washed sequentially with saturated sodium bisulfate solution (2.x.), saturated sodium bicarbonate solution, water, and brine; dried over sodium sulfate; and concentrated to afford 1.8 g (97percent) of 1,1-dimethylethyl 3-oxo-pyrrolidine-1-carboxylate: 1H-NMR (CDCl3) δ 3.75 (4H, m), 2.58 (2H, t, J=7.8 Hz), 1.49 (9H, s).To a solution of 3-hydroxy-pyrrolidine-1-carboxylic acid tert-b\xty\ ester (10 g, 54 mmol) in dichloromethane (300 mL) is added Dess-Martin Reagent (45.9 g, 108 mmol) in three portions. The resulting mixture is stirred for 16 hours. The mixture is filtered through CeIi te and the solvent removed in vacuo. The crude material is purified via silica gel chromatography using a gradient elution of 0-8percent ethyl acetate/hexanes to afford the desired product as a glassy solid (9.8 g, 97percent).A 3 L, four-necked round-bottomed flask was equipped with a mechanical stirrer, 500 mL addition funnel, cooling bath, K-type thermocouple and a nitrogen inlet. Oxalyl chloride (6.0 mL, 70.5 mmol) was added to 300 mL of DCM and cooled to - 78°C. DMSO (9.9 mL, 139mmol) was added thereto, and the mixture was stirred for 15 minutes. tert-butyl 3-hydroxypyrrolidin-1-carboxylate (8.98g, 48 mmol) obtained in Step A was added thereto, and the mixture was stirred for 20 minutes.
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