Potassium tert-butoxide → t-Butyl methyl-(4-cyanocyclohexyl)carbamate

HRID 1951020Notes

Reaction equation

HRID 1951020 reaction equation
[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].C1(C)C(S([CH2:26][N+:27]#[C-])(=O)=O)=CC=CC=1.CC(C)([O-])C.[K+]>O1CCCC1>[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][CH:13]([C:26]#[N:27])[CH2:12][CH2:11]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 24820328tert-butyl N-methyl-N-(4-oxocyclohexyl)carbamateHCID 53627694Toluenesulfonylmethyl isocyanide

Product 1

HCID 66725780t-Butyl methyl-(4-cyanocyclohexyl)carbamateYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

t-Butyl methyl-(4-oxocyclohexyl)carbamate (4.54 g, 20 mmol) and toluenesulphonylmethyl isocyanide (5.07 g, 26 mmol) were dissolved in dry tetrahydrofuran (100 ml) and cooled to 0° C. Potassium tert-butoxide (5.16 g, 46 mmol) was added slowly and the mixture was allowed to warm to 20° C. and stir for 3 hours. The reaction mixture was evaporated to dryness and partitioned between ethyl acetate (150 ml) and water (50 ml). The organic layer was separated, dried over magnesium sulfate and evaporated. The crude product was chromatographed on a silica gel eluting with ethyl acetate/hexane (66:34) to give 1.43 g of tert-butyl methyl-(4-cyanocyclohexyl)carbamate.

Workup

  1. temperatureto warm to 20° C.
  2. customThe reaction mixture was evaporated to dryness
  3. custompartitioned between ethyl acetate (150 ml) and water (50 ml)
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe crude product was chromatographed on a silica gel eluting with ethyl acetate/hexane (66:34)

Sources & evidence

ORD record
ord-420f1c6fd01f4bf79f6545c155e226f1
Source dataset
uspto-grants-2013_03
Patent number
US08404682B2

Reaction notes

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