Piperidine → HCID 18008062, compound

HRID 988248Notes

Reaction equation

HRID 988248 reaction equation
[C:1]([Si:5]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10](I)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:27]([OH:33])[CH2:28][CH2:29][CH2:30][C:31]#[CH:32].N1CCCCC1>C1COCC1.CCOCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[Si:5]([O:6][CH2:7][C:8]1[CH:9]=[C:10]([C:32]#[C:31][CH2:30][CH2:29][CH2:28][CH2:27][OH:33])[CH:11]=[CH:12][CH:13]=1)([C:1]([CH3:4])([CH3:3])[CH3:2])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

8

Reactant 3

HCID 8082PiperidineHCID 702345-Hexyn-1-olHCID 18008078HCID 18008078, compound

Product 1

HCID 18008062HCID 18008062, compoundYield 85.8%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of t-Butyl-diphenyl(3-iodo-benzyloxy)silane (8.49 g, 18 mmol) in THF (70 mL) is added hex-5-ynol (2.5 mL, 22 mmol) and (Ph3P)4Pd (990 mg, 0.85 mmol) and CuI (171 mg, 0.9 mmol). This solution is degassed and placed under an argon atmosphere. To this solution is added piperidine (5.4 mL, 54 mmol) and stirring continued for 4 h. The reaction mixture is diluted with ether, washed with water and brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (silica, 30% ethyl acetate in hexanes) to give the title compound as an oil (6.84 g). 1H NMR (300 MHz, CDCl3): δ 7.70 (m, 4H), 7.40 (m, 6H), 7.27 (m, 4H), 4.71 (s, 2H), 3.71 (t, 2H), 2.47 (t, 2H), 1.74 (m, 4H), 1.10 (s, 9H).

Workup

  1. customThis solution is degassed
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by flash chromatography (silica, 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9884b0d01171462786dd2f1490525866
Source dataset
uspto-grants-2003_10
Patent number
US06635655B1

Reaction notes

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