Sodium hydride → HCID 178453877, compound

HRID 500091

Reaction equation

HRID 500091 reaction equation
[H-].[Na+].[Br-].[CH:4]1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:6][CH2:5]1.[CH:26]([C@H:28]1[CH2:33][CH2:32][C@H:31]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:30][CH2:29]1)=O.COCCOCCN(CCOCCOC)CCOCCOC.[Cl-].[NH4+]>O1CCCC1>[C:4]1(=[CH:26][C@H:28]2[CH2:33][CH2:32][C@H:31]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:30][CH2:29]2)[CH2:6][CH2:5]1

Participants

7

Reactant 5

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 2723931Cyclopropyltriphenylphosphonium bromideHCID 178453955HCID 178453955, compound

Product 1

HCID 178453877HCID 178453877, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of sodium hydride (1.06 g) and anhydrous tetrahydrofuran (50 ml) was added cyclopropyl-triphenylphosphonium bromide (10.13 g), the mixture was heated under reflux for 1 hour. The reaction mixture was cooled to ambient temperature, and then thereto was added a mixture of t-butyl trans-4-formylcyclohexylcarbamate (3.00 g), tris[2-(2-methoxyethoxy)ethyl]amine (427 mg) and anhydrous tetrahydrofuran (15 ml). The resulting mixture was heated under reflux for 1 hour. The reaction mixture was cooled to ambient temperature, and then saturated aqueous ammonium chloride was added to the reaction mixture. The reaction mixture was extracted with ethyl acetate, the organic layer was washed with brine, dried over sodium sulfate, and then the solvent was removed in vacuo. The residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate) to give 1.43 g of t-butyl trans-4-cyclopropylidenemethylcyclohexylcarbamate.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. additionwas added
  4. temperatureThe resulting mixture was heated
  5. temperatureunder reflux for 1 hour
  6. temperatureThe reaction mixture was cooled to ambient temperature
  7. extractionThe reaction mixture was extracted with ethyl acetate
  8. washthe organic layer was washed with brine
  9. dry with materialdried over sodium sulfate
  10. customthe solvent was removed in vacuo
  11. customThe residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate)

Sources & evidence

ORD record
ord-9270142efa654b0cbefa7320fe97f2c8
Source dataset
uspto-grants-2010_08
Patent number
US07767854B2

Linked notes

Loading…