Triethylamine → HCID 58495570, compound

HRID 1190985Notes

Reaction equation

HRID 1190985 reaction equation
[CH:1]1([C:7]#[CH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]([O:13][C:14]([NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(N(CC)CC)C>CN(C=O)C.O.CCCCCC.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:9]([O:13][C:14]([NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:8]#[C:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:20][CH:19]=1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

9

Reactant 3

HCID 8471TriethylamineHCID 70263EthynylcyclohexaneHCID 12453839tert-butyl N-[(4-bromophenyl)methyl]carbamate

Product 1

HCID 58495570HCID 58495570, compoundYield 34.7%

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Add cyclohexylacetylene (1.1 mL, 8.4 mmol) to a slurry of N-(tert-butoxycarbonyl)-4-bromo-benzylamine (2 g, 6.9 mmol), dichlorobis(triphenylphosphine)palladium (147 mg, 0.2 mmol), copper(I) iodide (67 mg, 0.4 mmol) and triethylamine (1.4 mL, 9.7 mmol) in DMF (7 mL). Stir the reaction in a sealed flask at 110° C. for 16 h. Cool to room temperature, dilute with water (10 mL) and hexane/EtOAc (1:1, 100 mL). Filter the bi-phasic mixture through Celite®, collect the organic phase and wash with 5% aqueous NaCl (3×30 mL). Concentrate the organic phase in vacuo and purify by chromatography on silica gel (120 g) eluting with hexane/EtOAc (20:1 to 3:2 gradient) to obtain the desired intermediate (0.75 g, 34%). MS (ES+) m/z: 258 [M-(t-Bu)+H]+.

Workup

  1. customthe reaction in a sealed flask at 110° C. for 16 h
  2. filtrationFilter the bi-phasic mixture through Celite®
  3. customcollect the organic phase
  4. washwash with 5% aqueous NaCl (3×30 mL)
  5. concentrationConcentrate the organic phase in vacuo
  6. custompurify by chromatography on silica gel (120 g)
  7. washeluting with hexane/EtOAc (20:1 to 3:2 gradient)

Sources & evidence

ORD record
ord-08848363b3024a7a8ad74dccacd41807
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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