(R)-1-Boc-3-cyanopyrrolidine synthesis

6synthesis methods

Product Name:(R)-1-Boc-3-cyanopyrrolidine
CAS Number:132945-76-7
Molecular formula:C10H16N2O2
Molecular Weight:196.25

143-33-9 Synthesis

143-33-9
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$10.00/1g

132945-75-6 Synthesis

(S)-1-Boc-3-methanesulfonyloxy-pyrrolidine

132945-75-6
47 suppliers
$9.00/250mg

132945-76-7
119 suppliers
$21.00/250mg

Yield: 39%

Reaction Conditions:

in dimethyl sulfoxide at 80; for 4 h;

Steps:

29
Powdered sodium cyanide (550 mg, 1.3 mmol) was added to a solution of TERT- butyl (3S)-3-[(METHYLSULFONYL) oxy] pyrrolidine-1-carboxylate (2.0 g, 7.54 mmol) in DMSO (10 ml) and the reaction mixture heated at 80°C for 4 hours. The resulting yellow mixture was cooled and brine (4 ml) and water (4.5 ml) were added. The mixture was extracted with diethyl ether (x3), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residues were purified by flash chromatography on SI02 eluting with diethylether/isohexane (50/50) to give TERT-BUTYL (3R)-3-cyanopyrrolidine-1- CARBOXYLATE AS A COLOURLESS OIL (579MG, 39%) ; 1H NMR SPECTRUM: (DMSOD6) 1.39 (S, 9H); 2.08 (m, 1H); 2. 18 (m, 1H); 3. 34 (m, 4H); 3.53 (m, 1H).

References:

ASTRAZENECA AB;ASTRAZENEKA UK LIMITED WO2005/26156, 2005, A1 Location in patent:Page/Page column 117

773837-37-9 Synthesis