Hydrochloric Acid → HCID 58860597, compound

HRID 1350438Notes

Reaction equation

HRID 1350438 reaction equation
C12BC(CCC1)CCC2.[CH2:10]([N:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19][C@@H:18]1[CH:30]=[CH2:31])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.I[C:52]1[CH:56]=[CH:55][S:54][CH:53]=1.[OH-].[Na+].Cl>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:10]([N:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19][C@@H:18]1[CH2:30][CH2:31][C:52]1[CH:56]=[CH:55][S:54][CH:53]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 663323-IodothiopheneHCID 789669-Borabicyclo(3.3.1)nonaneHCID 17759473(S)-1,4-dibenzyl-2-vinylpiperazine

Product 1

HCID 58860597HCID 58860597, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

Combine 9-borabicyclo[3.3.1]nonane (54.7 mL, 27.4 mmol, 0.5 M in THF) and (S)-1,4-dibenzyl-2-vinyl-piperazine (2.0 g, 6.84 mmol) and stir at ambient temperature. After 24 h, add triphenylphosphine (574 mg, 2.2 mmol), tetrakis(triphenylphosphine) palladium(0) (316 mg, 0.27 mmol) and 3-iodothiophene (1.93 g, 9.2 mmol). Add 3M NaOH (5.6 mL, 16.8 mmol) slowly, gas evolution occurs. Heat at reflux. After 48 h, cool to ambient temperature, add 5N HCl (12 mL), and stir 1 h. Extract with ethyl acetate and wash the extracts with 1N NaOH, water, brine, dry over sodium sulfate, filter and concentrate. Purify by silica gel chromatography using ethyl acetate/hexanes (10%) as the eluent to give 2.38 g of the title compound as an adduct of 9-BBN: mass spectrum (ion spray): m/z=377 (M+1).

Workup

  1. temperatureHeat
  2. temperatureat reflux
  3. waitAfter 48 h
  4. extractionExtract with ethyl acetate
  5. washwash the extracts with 1N NaOH, water, brine
  6. dry with materialdry over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-b948f30d56d94cb3a539547fde2875c2
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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