Stannous Chloride → cis-(6-Benzhydryl-tetrahydropyran-3-yl)-(4-amino-benzyl)-amine

HRID 606986Notes

Reaction equation

HRID 606986 reaction equation
[CH:1]([C@H:14]1[O:19][CH2:18][C@@H:17]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=2)[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[Sn]Cl.CCOC(C)=O.CCN(CC)CC>CCO.CCOC(C)=O>[CH:1]([C@H:14]1[O:19][CH2:18][C@@H:17]([NH:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([NH2:28])=[CH:26][CH:27]=2)[CH2:16][CH2:15]1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 11531477Cis-(6-benzhydryl-tetrahydropyran-3-yl)-(4-nitro-benzyl)-amineHCID 22036596Ethyl acetate triethylamine

Product 1

HCID 11510954cis-(6-Benzhydryl-tetrahydropyran-3-yl)-(4-amino-benzyl)-amineYield 60%

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

A mixture of cis-(6-benzhydryl-tetrahydropyran-3-yl)-(4-nitro-benzyl)-amine (16f) (0.16 g, 0.39 mmol) and SnCl2/2H2O (0.35 g, 1.55 mmol) in EtOH/EtOAc (20 ml, 7:3) was heated to reflux for 1.5 h (monitored by TLC, Hex/EtOAc/Et3N 5:5:0.4). After removal of the solvent, the residue was diluted with 10% NaHCO3 and EtOAc and stirred vigorously for 30 min. After filtration the organic phase was separated and the aqueous phase was extracted with EtOAc (20 ml×2). The combined organic phase was dried over Na2SO4. After removal of the solvent, flash chromatography gave 16o, cis-(6-benzhydryl-tetrahydropyran-3-yl)-(4-amino-benzyl)-amine (0.087 g, 60%).

Workup

  1. temperaturewas heated
  2. customAfter removal of the solvent
  3. additionthe residue was diluted with 10% NaHCO3 and EtOAc
  4. filtrationAfter filtration the organic phase
  5. customwas separated
  6. extractionthe aqueous phase was extracted with EtOAc (20 ml×2)
  7. dry with materialThe combined organic phase was dried over Na2SO4
  8. customAfter removal of the solvent, flash chromatography

Sources & evidence

ORD record
ord-d4f721048cf94f49811e19153877980c
Source dataset
uspto-grants-2011_03
Patent number
US07915433B2

Reaction notes

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