Sodium Sulfate → trans-2-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-amine

HRID 501699Notes

Reaction equation

HRID 501699 reaction equation
[CH2:1]([O:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:14][CH3:15])=[CH:10][CH:11]=2)[CH:6]1[N:16]=[N+]=[N-])[CH:2]=[CH2:3].[H-].[H-].[H-].[H-].[Li+].[Al+3].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH2:1]([O:4][C@@H:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:14][CH3:15])=[CH:10][CH:11]=2)[C@H:6]1[NH2:16])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 86622331(1RS,2RS)-2-(allyloxy)-1-azido-6-methoxy-2,3-dihydro-1H-indene

Product 1

HCID 59423690trans-2-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step AA (6): To a solution of (1RS,2RS)-2-(allyloxy)-1-azido-6-methoxy-2,3-dihydro-1H-indene from Step AA (5) (71 mg) in THF (4 mL) at rt was added LiAlH4 (33 mg), and the resulting suspension was stirred at rt for 10 min. Five crystals of Na2SO4.10H2O was added followed by anhydrous sodium sulfate, and the reaction mixture was stirred at rt for 30 min and filtered through a pad of Celite. The filtrate was evaporated in vacuo to give the title compound as a slightly yellowish oil (53 mg). retention time: 1.31 min (method A). MS (ESI) (M+H)+ 220.15.

Workup

  1. stirringthe reaction mixture was stirred at rt for 30 min
  2. filtrationfiltered through a pad of Celite
  3. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-10720298042f447f9607135decb679f4
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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