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

HRID 425188Notes

Reaction equation

HRID 425188 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-5757e6e1e25b4119ab787ec242b2142f
Source dataset
uspto-grants-2012_01
Patent number
US08106057B2

Reaction notes

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