Sodium Cyanide → HCID 178483638, compound

HRID 1063647Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([CH3:23])[CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17]OS(C)(=O)=O)[CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C-:24]#[N:25].[Na+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][C:24]#[N:25])[CH2:13][CH2:12]1)[CH3:23])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To 12.64 g (36.17 mmol) of trans-methanesulfonic acid 4-[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-cyclohexylmethyl ester in 100 mL of DMF were added 4.51 g (92 mmol, 2.6 eq) of sodium cyanide, and the solution was stirred at 80° C. for 2 hours. After cooling the reaction mixture to RT, it was partitioned between ether and water. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give 10.14 g (quantitative) of crude trans-[2-(4-cyanomethyl-cyclohexyl)-ethyl]-methyl-carbamic acid tert-butyl ester as colorless oil, MS: 298 (M+NH4+).

Workup

temperatureAfter cooling the reaction mixture to RT
customit was partitioned between ether and water
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-c39758bcb2c24f8c9c607804f58bff3e
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06965048B2

Reaction notes

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