Hexane → HCID 18922011, compound

HRID 1289809Notes

Reaction equation

HRID 1289809 reaction equation
O=C(C)CC[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13](=[O:26])[C:14]([CH:22]2[CH2:25][CH2:24][CH2:23]2)([OH:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:8][CH2:7]1.[CH2:28]([Li])[CH2:29][CH2:30][CH3:31].[CH3:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C>[CH3:31]/[C:30](=[CH:33]/[CH3:34])/[CH2:29][CH2:28][CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13](=[O:26])[C:14]([CH:22]2[CH2:23][CH2:24][CH2:25]2)([OH:21])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:8][CH2:7]1.[CH3:28]/[C:35](=[CH:34]\[CH3:33])/[CH2:36][CH2:37][CH2:38][N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13](=[O:26])[C:14]([CH:22]2[CH2:23][CH2:24][CH2:25]2)([OH:21])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 8058HexaneHCID 18922085HCID 18922085, compoundHCID 178418339Butyllithium

Product 2

HCID 18922011HCID 18922011, compoundHCID 69831569HCID 69831569, compound

Reagents, catalysts & solvents 1

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)Catalyst

Conditions

Temperature
0 °C

Procedure

62 mg of N-[1-(4-oxopentyl)piperidin-4-yl]-2-cyclobutyl-2-hydroxy-2-phenylacetamide was added at 0° C. to an ylide compound prepared from 124 mg of ethyltriphenylphosphonium bromide and 200 μl of n-butyl lithium (as a 1.62M hexane solution), and this mixture was stirred at 0° C. for 30 minutes and then at room temperature for 4 hours. After the solvent was distilled off under reduced pressure, the resulting residue was mixed with 20 ml of water and then extracted with chloroform (30 ml×3). The organic layer was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by preparative thin-layer chromatography [Kieselgel™ 60F254, Art 5744 (manufactured by E. Merck); developing solvent: chloroform to chloroform/methanol=10/1) to obtain 18.0 mg of N-[1-(Z)-(4-methyl-4-hexenyl)piperidin-4-yl]-2-cyclobutyl-2-hydroxy-2-phenylacetamide and 9.0 mg of N-[1-(E)-(4-methyl-4-hexenyl)piperidin-4-yl]-2-cyclobutyl-2-hydroxy-2-phenylacetamide.

Workup

  1. waitat room temperature for 4 hours
  2. distillationAfter the solvent was distilled off under reduced pressure
  3. additionthe resulting residue was mixed with 20 ml of water
  4. extractionextracted with chloroform (30 ml×3)
  5. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationAfter the solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified by preparative thin-layer chromatography [Kieselgel™ 60F254, Art 5744 (manufactured by E. Merck)

Sources & evidence

ORD record
ord-6b41e0a8e22a4eb0b27c7dd06579cd5d
Source dataset
uspto-grants-1998_05
Patent number
US05750540

Reaction notes

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