Stannous chloride dihydrate → (5-Amino-1,3-dihydro-isoindol-2-yl)-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-methanone

HRID 2355721Notes

Reaction equation

HRID 2355721 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([CH:23]([CH3:25])[CH3:24])=[CH:11][C:10]=1[C:26]([N:28]1[CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([N+:37]([O-])=O)[CH:34]=2)[CH2:29]1)=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl>C(O)C>[NH2:37][C:33]1[CH:34]=[C:35]2[C:30](=[CH:31][CH:32]=1)[CH2:29][N:28]([C:26]([C:10]1[CH:11]=[C:12]([CH:23]([CH3:25])[CH3:24])[C:13]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:27])[CH2:36]2

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 66672501(2,4-Bis-benzyloxy-5-isopropyl-phenyl)-(5-nitro-1,3-dihydro-isoindol-2-yl)methanone

Product 1

HCID 66672407(5-Amino-1,3-dihydro-isoindol-2-yl)-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-methanoneYield 87.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (2,4-bis-benzyloxy-5-isopropyl-phenyl)-(5-nitro-1,3-dihydro-isoindol-2-yl)methanone (460 mg; 0.88 mmol) in ethanol (25 ml) was treated with tin (II) chloride dihydrate (1 g; 5 equiv.) then heated at reflux overnight then evaporated in vacuo. The residue was partitioned between EtOAc and saturated NaHCO3, the EtOAc layer was separated, dried (MgSO4) and evaporated to give 380 mg of (5-amino-1,3-dihydro-isoindol-2-yl)-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-methanone.

Workup

  1. temperaturethen heated
  2. temperatureat reflux overnight
  3. customthen evaporated in vacuo
  4. customThe residue was partitioned between EtOAc and saturated NaHCO3
  5. customthe EtOAc layer was separated
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-f03d260b5deb4847a111fd32dec0f014
Source dataset
uspto-grants-2010_07
Patent number
US07754725B2

Reaction notes

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