2-Aminoindane-2-carboxylic acid → (2-Amino-2,3-dihydro-1H-inden-2-yl)methanol

HRID 19725Notes

Reaction equation

HRID 19725 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1([C:17](O)=[O:18])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1>CCOCC>[NH2:7][C:8]1([CH2:17][OH:18])[CH2:9][C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:16]1

Participants

4

Reactant 2

HCID 2509362-Aminoindane-2-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 22080542(2-Amino-2,3-dihydro-1H-inden-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Lithium aluminium hydride (1 M solution in ether, 23.7 ml, 23.7 mmol) is added to a solution of 2-aminoindan-2-carboxylic acid (J. Med. Chem. 1991, 34, 3125; 2.26 g, 12.8 mmol) in ether (150 ml). The reaction is stirred for 2 hours at ambient temperature and quenched sequentially with water (0.9 ml), 2 M NaOH (0.9 ml) and further water (0.9 ml). MgSO4 is added and the resultant suspension is filtered. The filtrate is evaporated to afford (2-aminoindan-2-yl)methanol, MH+164.

Workup

  1. customquenched sequentially with water (0.9 ml), 2 M NaOH (0.9 ml) and further water (0.9 ml)
  2. additionMgSO4 is added
  3. filtrationthe resultant suspension is filtered
  4. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-8a4b4d64cbaa41c1a528cfed78cf142d
Source dataset
uspto-grants-2010_06
Patent number
US07745462B2

Reaction notes

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