Sodium Cyanide → 3-(1-Adamantyl)propanenitrile

HRID 1925511

Reaction equation

CS(O[CH2:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)(=O)=O.[C-:18]#[N:19].[Na+]>CS(C)=O>[C:8]12([CH2:7][CH2:6][C:18]#[N:19])[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of Intermediate 44 (4.1 g, 16.01 mmol) in dimethyl sulfoxide (18 mL) was slowly added sodium cyanide (0.98 g, 20 mmol). The reaction mixture was stirred at 100° C. for 1.5 hours and at room temperature overnight. The crude was partitioned between ether and water and the organic layer was washed with water. The solvent was removed under reduced pressure and the title compound was obtained as a colourless solid (2.9 g, 98%) and used in the next step without further purification.

Workup

customThe crude was partitioned between ether and water
washthe organic layer was washed with water
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-7ce11a9a6b6f40e48157489bb09fe894
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178679B2

Linked notes

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