Hydrogen Bromide → (1S,2R)-(-)-1-Amino-2-indanol

HRID 1861135Notes

Reaction equation

HRID 1861135 reaction equation
O[C@@H]1CC2C(=CC=CC=2)C1=O.C(O[C@H](CC1C=CC=CC=1)C(O)=O)(=O)C.[OH:27][CH:28]1[CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]1=[N:37]O.Br>[Pd]>[NH2:37][C@H:29]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:36][C@H:28]1[OH:27]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 11137320(R)-2-hydroxy-1-indanone2×HCID 11469837(R)-2-acetoxy-3-phenylpropanoic acidHCID 713473561-(Hydroxyimino)-2,3-dihydro-1H-inden-2-ol

Product 1

HCID 9866743(1S,2R)-(-)-1-Amino-2-indanol

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Kajiro et al., Bull. Chem. Soc. Jap. 1999, 72: 1093-1100, discloses the preparation of (R)-2-hydroxy-1-indanone by the intramolecular Friedel-Crafts acylation of (R)-2-acetoxy-3-phenylpropanoic acid. Kajiro et al. further discloses the preparation of the corresponding hydroxyindanone oxime from (R)-2-hydroxy-1-indanone, and then hydrogenating the oxime in the presence of HBr and Pd black to obtain (1S,2R)-1-amino-2-indanol.

Sources & evidence

ORD record
ord-d213080fe2ce48179708416fc55c233d
Source dataset
uspto-grants-2003_03
Patent number
US06531617B2

Reaction notes

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