Sodium Cyanide → HCID 178453919, compound

HRID 1257708Notes

Reaction equation

HRID 1257708 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15]OS(C)(=O)=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C-:21]#[N:22].[Na+]>CS(C)=O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][C:21]#[N:22])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 178453973HCID 178453973, compound

Product 1

HCID 178453919HCID 178453919, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of trans methanesulfonic acid 4-tert-butoxycarbonylamino-cyclohexylmethyl ester (0.93 mg, 3.00 mmol) and sodium cyanide (0.44 g, 9.00 mmol) in DMSO (10 mL) was stirred at 90° C. for 4 hours. After cooling the mixture was partitioned between ethyl acetate and brine and the aqueous phase was extracted with ethyl acetate (×2). The combined organic extracts were washed with water, brine, dried with sodium sulfate and concentrated under vacuum to give 0.72 g (100%) of trans (4-cyanomethyl-cyclohexyl)-carbamic acid tert-butyl ester as a white solid. 1H NMR (400 MHz, CDCl3) δ: 4.38 (br s, 1H), 3.45-3.33 (m, 1H), 2.26 (d, 2H), 2.10-2.02 (m, 2H), 1.96-1.87 (m, 2H), 1.71-1.57 (m, 1H), 1.45 (s, 9H), 1.26-1.03 (m, 4H).

Workup

  1. temperatureAfter cooling the mixture
  2. customwas partitioned between ethyl acetate and brine
  3. extractionthe aqueous phase was extracted with ethyl acetate (×2)
  4. washThe combined organic extracts were washed with water, brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2037812c506548e399cd165fb1a75a2d
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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