Stannous chloride dihydrate → HCID 70024844, compound

HRID 1358468Notes

Reaction equation

HRID 1358468 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([N+:28]([O-])=O)=[C:13]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[CH:14]=2)[CH:9]1[CH2:31][C:32]1[CH:37]=[C:36]([Br:38])[C:35]([O:39][CH3:40])=[C:34]([Br:41])[CH:33]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.O.[Sn](Cl)Cl>C(OCC)(=O)C.N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([NH2:28])=[C:13]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[CH:14]=2)[CH:9]1[CH2:31][C:32]1[CH:33]=[C:34]([Br:41])[C:35]([O:39][CH3:40])=[C:36]([Br:38])[CH:37]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 70024652HCID 70024652, compound

Product 1

HCID 70024844HCID 70024844, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 1-(3,5-dibromo-4-methoxybenzyl)-6-(4-methoxy-benzyloxy)-7-nitro-1,2,3,4-tetrahydro-isoquinoline-2-carboxylic acid tert-butyl ester (8.31 g, 0.012 mol) in 120 mL of ethyl acetate and 12 mL of pyridine was added powder tin (II) chloride dihydrate (27.08 g, 0.12 mol). The reaction mixture was stirred for 5 h at 55° C., cooled and filtered. The filtrate was washed 2 times with 1N NaOH. Water phase was extracted with chloroform. The extracts and ethyl acetate solution were combined, dried over Na2SO4 and concentrated. The product was purified by column chromatography (silica gel, ethyl acetate-hexanes mixture (1:4)), evaporated with ethyl ether and dried in vacuum. Yield 4.864 g (61%).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. washThe filtrate was washed 2 times with 1N NaOH
  4. extractionWater phase was extracted with chloroform
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe product was purified by column chromatography (silica gel, ethyl acetate-hexanes mixture (1:4))
  8. customevaporated with ethyl ether
  9. customdried in vacuum

Sources & evidence

ORD record
ord-83f0065becda4f76ae75fc371d9bf7cd
Source dataset
uspto-grants-2003_07
Patent number
US06596734B1

Reaction notes

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