1,4-Dioxane → (1R,2R)-2-Amino-2,3-dihydro-1H-inden-1-ol

HRID 722271Notes

Reaction equation

HRID 722271 reaction equation
[C:1]1(=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[N:10]O.O1CCOCC1>CCO>[NH2:10][C@@H:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C@H:1]1[OH:12]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 63990382-Oximino-1-indanone

Product 1

HCID 10898857(1R,2R)-2-Amino-2,3-dihydro-1H-inden-1-olYield 171.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of indan-1,2-dione-2-oxime (6.2g, 39mmol) in EtOH (470 ml) and 4MHCl/Dioxane (36 ml) was hydrogenated at room temperature and 40 psi. The reaction mixture was filtered through celite, washed with EtOH (30 ml) and concentrated under reduced pressure to give 10 g of an off-white solid which was recrystallised from EtOH to give the title compound (5 g, 86%) as a white solid.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe reaction mixture was filtered through celite
  3. washwashed with EtOH (30 ml)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9aecac21b87c419eb310ab727ccb8096
Source dataset
uspto-grants-2006_11
Patent number
US07138415B2

Reaction notes

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