Ammonium Chloride → HCID 178444562, compound

HRID 500071Notes

Reaction equation

HRID 500071 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C(C)C.[CH:31]([C@H:33]1[CH2:38][CH2:37][C@H:36]([NH:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[CH2:35][CH2:34]1)=O.[Cl-].[NH4+]>CN(C)C=O>[CH3:1][CH:2]([CH3:5])/[CH:3]=[CH:31]\[C@H:33]1[CH2:38][CH2:37][C@H:36]([NH:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 2724571Isobutyltriphenylphosphonium bromideHCID 23665647Potassium tert-butoxideHCID 178453955HCID 178453955, compound

Product 1

HCID 178444562HCID 178444562, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of potassium t-butoxide (379 mg) and anhydrous N,N-dimethylformamide (20 ml) was added isobutyltriphenylphosphonium bromide (1.35 g) at room temperature. The mixture was stirred for 10 minutes, and then a solution of t-butyl trans-4-formylcyclohexyl-carbamate (700 mg) in N,N-dimethylformamide (3 ml) was added to the mixture. After the reaction mixture was stirred overnight, saturated aqueous ammonium chloride was added thereto. The mixture was extracted with toluene, and the organic layer was washed with brine, dried over sodium sulfate, and then the solvent was removed in vacuo. After diethyl ether was added to the residue, the precipitate was filtered off and then the filtrate was concentrated under reduced pressure. 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 380 mg of t-butyl trans-{4-[(Z)-3-methyl-1-butenyl]cyclohexyl}-carbamate.

Workup

  1. stirringAfter the reaction mixture was stirred overnight
  2. extractionThe mixture was extracted with toluene
  3. washthe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was removed in vacuo
  6. additionAfter diethyl ether was added to the residue
  7. filtrationthe precipitate was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. 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-9735f939695a48cbb67f845df367ead8
Source dataset
uspto-grants-2010_08
Patent number
US07767854B2

Reaction notes

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