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ChemicalBook CAS DataBase List (R)-1-Boc-3-cyanopyrrolidine
132945-76-7

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

6synthesis methods
143-33-9 Synthesis
Sodium cyanide

143-33-9
5 suppliers
$10.00/1g

132945-75-6 Synthesis
(S)-1-Boc-3-methanesulfonyloxy-pyrrolidine

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

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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
sodium:cyanide

773837-37-9
0 suppliers
inquiry

132945-75-6 Synthesis
(S)-1-Boc-3-methanesulfonyloxy-pyrrolidine

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

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