Dimethylformamide → HCID 86629083, compound

HRID 500070

Reaction equation

HRID 500070 reaction equation
C[C:2]([CH3:5])([O-])[CH3:3].[K+].O=[C:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:10][CH2:9]1.[Cl-].[NH4+].[CH3:24]N(C)C=O>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CCC>[CH:24](=[C:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:10][CH2:9]1)[CH2:3][CH2:2][CH3:5]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 25517Ammonium ChlorideHCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamateHCID 23665647Potassium tert-butoxide

Product 1

HCID 86629083HCID 86629083, compound

Reagents, catalysts & solvents 1

HCID 159628Butyltriphenylphosphonium bromideCatalyst

Procedure

To a mixture of potassium t-butoxide (2.05 g) and anhydrous N,N-dimethylformamide (60 ml) was added butyltriphenylphosphonium bromide (7.30 g) at room temperature. The mixture was stirred for 15 minutes and then a solution of t-butyl 4-oxocyclohexylcarbamate (1.30 g) in N,N-dimethylformamide (10 ml) was added to the mixture. The reaction mixture was stirred at room temperature overnight and then saturated aqueous ammonium chloride was added to the mixture. 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 1.40 g of t-butyl (4-butylidenecyclohexyl)carbamate.

Workup

  1. stirringThe reaction mixture was stirred at room temperature 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-1fa0f1a583cb4d2886f66a95cb1ac0bd
Source dataset
uspto-grants-2010_08
Patent number
US07767854B2

Linked notes

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