Isopropylamine → HCID 68616172, compound

HRID 1158479Notes

Reaction equation

HRID 1158479 reaction equation
[CH2:1]([N:8]1[CH2:12][C@@H:11]2[CH2:13][O:14][C:15](=[O:16])[C@@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]([NH2:20])([CH3:19])[CH3:18]>[Cl-].[Cl-].[Zn+2]>[CH:17]([NH:20][C:15]([C@H:10]1[C@@H:11]([CH2:13][OH:14])[CH2:12][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9]1)=[O:16])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 51387247HCID 51387247, compound

Product 1

HCID 68616172HCID 68616172, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

A suspension of (3aR*,6aS*)-5-benzyl-hexahydro-furo[3,4-c]pyrrol-1-one (1.50 g, 6.90 mmol) and ZnCl2 (0.94 g, 6.90 mmol) in iPrNH2 (20 mL) is refluxed overnight under a nitrogen atmosphere. The crude material is filtered over a pad of Celite and concentrated. The crude material is purified by flash chromatography on silica gel (eluent: CH2Cl2/MeOH/NH4OH 70:25:5) to give the title product. TLC, Rf (CH2Cl2/MeOH 95:5)=0.38. MS (LC-MS): 277.2 [M+H]+.

Workup

  1. temperatureis refluxed overnight under a nitrogen atmosphere
  2. filtrationThe crude material is filtered over a pad of Celite
  3. concentrationconcentrated
  4. customThe crude material is purified by flash chromatography on silica gel (eluent: CH2Cl2/MeOH/NH4OH 70:25:5)

Sources & evidence

ORD record
ord-a761c504a6a14b6ebe716f1fa0964d99
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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