Potassium bis(trimethylsilyl)amide → HCID 86596944, compound

HRID 2225240Notes

Reaction equation

HRID 2225240 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[K+].[C:11]([O:15][C:16](=[O:38])[NH:17][C@@H:18]1[CH2:23][CH2:22][C@H:21]([NH:24][C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[C@H:20]([C:35](=O)[CH3:36])[CH2:19]1)([CH3:14])([CH3:13])[CH3:12]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.C1(C)C=CC=CC=1>[CH2:28]([O:27][C:25]([NH:24][C@H:21]1[CH2:22][CH2:23][C@@H:18]([NH:17][C:16](=[O:38])[O:15][C:11]([CH3:13])([CH3:12])[CH3:14])[CH2:19][C@H:20]1[C:35]([CH3:36])=[CH2:1])=[O:26])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 69286629HCID 69286629, compound

Product 1

HCID 86596944HCID 86596944, compound

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Methyltriphenylphosphoniumbromide (729 mg) was dissolved in THF (4 mL) and cooled to 0° C. prior to the addition of 0.5M potassium bis(trimethylsilyl)amide (3.7 mL) in toluene. After 1 h, (1R,3R,4S)-(4-benzyloxycarbonylamino-3-acetylcyclohexyl)carbamic acid tert-butyl ester (400 mg) in THF (4 mL) was added dropwise. The reaction was warmed to rt over 2 h, before it was quenched with saturated NH4Cl solution and extracted with EtOAc (3×) The organic extracts were combined, washed with brine, dried (Na2SO4), filtered, and concentrated. The resulting residue was purified by flash chromatography to provide tert-butyl (1R,3S,4S)-4-benzyloxycarbonylamino-3-(prop-1-en-2-yl)cyclohexylcarbamate (380 mg). MS (ES+)=389.2 (M+H)+.

Workup

  1. temperatureThe reaction was warmed to rt over 2 h, before it
  2. customwas quenched with saturated NH4Cl solution
  3. extractionextracted with EtOAc (3×) The organic extracts
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-bf30850523664536a4e5ceb3d6e7a1f5
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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