Sodium Cyanide → 1-Benzylpyrrolidine-3-carbonitrile

HRID 491510

Reaction equation

S([O-])(=O)(=O)C.[CH2:6]([N:13]1[CH2:17][CH2:16][CH:15](O)[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C-:19]#[N:20].[Na+]>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O>[CH2:6]([N:13]1[CH2:17][CH2:16][CH:15]([C:19]#[N:20])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 82.5 °C

Procedure

This transformation was carried out using the method described in C. Thomas et. al. reference 97. The mesylate of racemic 1-benzyl-pyrrolidin-3-ol (0.039 mol, 10 g), prepared as described above, sodium cyanide (0.24 mol, 15 g) and tetrabutylammonium cyanide (10 g, 0.037 mol) in 75 mL of DMSO was stirred at 80-85° C. for 16 h. The reaction mixture was partitioned between diethyl ether and sat. aq sodium bicarbonate. The aqueous layer was extracted twice with ether and the combined organic layer was washed successively with sodium bicarbonate, water, and sat aq. NaCl. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and purified by flash chromatography over silica gel using a gradient of 20 to 30% ethyl acetate in hexane to afford 5.5 g of the desired product.

Workup

customThe reaction mixture was partitioned between diethyl ether and sat. aq sodium bicarbonate
extractionThe aqueous layer was extracted twice with ether
washthe combined organic layer was washed successively with sodium bicarbonate, water
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated
custompurified by flash chromatography over silica gel using a gradient of 20 to 30% ethyl acetate in hexane

Sources & evidence

ORD record: ord-178c84c80efa45d59f6e2a8c7ccc7419
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531552B2

Linked notes

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