Tributylstannane → Hydrochloric Acid

HRID 1360009Notes

Reaction equation

HRID 1360009 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]=[C:11]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2I)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(N=NC(C#N)(C)C)(C#N)C.CCCC[SnH](CCCC)CCCC>C1C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=3[O:15][CH2:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:22]

Participants

6

Reactant 3

HCID 5948Tributylstannane2×HCID 6547Azobisisobutyronitrile2×HCID 59598938HCID 59598938, compound

Product 2

HCID 313Hydrochloric AcidHCID 59433646HCID 59433646, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a refluxing solution of 1-benzyl-4-(4-chloro-2-iodo-phenoxymethyl)-1,2,3,6-tetrahydro-pyridine 4c (26.7 g, 0.06 mol) and AIBN (0.05 g, 0.003 mol) in dry benzene was added a solution of Bu3SnH (40 g, 0.137 mol) in benzene (100 mL) over 1 h under nitrogen atmosphere. After addition, the mixture was refluxed for 3 hr and additional AIBN (0.5 g, 0.003 mol) and Bu3SnH (20 g, 0.68 mol) were added. After refluxing for 4 hr, the mixture was concentrated to dryness, and EtOAc (100 mL) and HCl (10%, 40 mL) were added. The precipitate was filtered and washed with petroleum ether to give 2,3-dihydro-1′-benzyl-5-chlorospiro (benzofuran-3,4′-piperidine) as its HCl salt, which was basified by NaHCO3 solution to give 2,3-dihydro-1′-benzyl-5-chlorospiro (benzofuran-3,4′-piperidine) 4d (13 g, 68%).

Workup

  1. additionAfter addition
  2. temperaturethe mixture was refluxed for 3 hr
  3. temperatureAfter refluxing for 4 hr
  4. concentrationthe mixture was concentrated to dryness, and EtOAc (100 mL) and HCl (10%, 40 mL)
  5. additionwere added
  6. filtrationThe precipitate was filtered
  7. washwashed with petroleum ether

Sources & evidence

ORD record
ord-0f01ff51ed4a4d98b862399573b50cee
Source dataset
uspto-grants-2011_02
Patent number
US07879834B2

Reaction notes

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