Trimethylsilyldiazomethane → 4-Amino-indan-5-carboxylic acid methyl ester

HRID 2353935Notes

Reaction equation

HRID 2353935 reaction equation
[NH2:1][C:2]1[C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH2:6]2.[CH3:14][Si](C=[N+]=[N-])(C)C>C(OCC)(=O)C.C(O)C>[CH3:14][O:12][C:11]([C:10]1[C:2]([NH2:1])=[C:3]2[C:7](=[CH:8][CH:9]=1)[CH2:6][CH2:5][CH2:4]2)=[O:13]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 148855494-Aminoindane-5-carboxylic Acid

Product 1

HCID 593791394-Amino-indan-5-carboxylic acid methyl esterYield 76%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add 30% aqueous hydrogen peroxide solution (5 mL) in water (44 mL) to a solution of 1,6,7,8-Tetrahydro-1-aza-as-indacene-2,3-dione (3.80 mg, 20.3 mmol) and sodium hydroxide (5.03 g, 126 mmol) in water (97 μL) over a period of 30 minutes, stir the mixture at room temperature for 1 h. Acidulate with 1N hydrochloric acid, filter the solid, wash with water and dry to afford 4-Amino-indan-5-carboxylic acid (3.13 g, 87%). Dissolve 4-Amino-indan-5-carboxylic acid (3.07 g, 17.3 mmol) in ethyl acetate (87 mL) and ethanol (87 mL) and add (trimethylsilyl) diazomethane (17.3 mL, 34.6 mmol, 2M in hexanes) at room temperature and stir the solution for 1 hour. Remove the solvent under reduced pressure. Purify the residue by flash chromatography, eluting with hexanes/ethyl acetate, to afford the title compound (2.50 g, 76%). 1H NMR (MeOD, 300 MHz) δ 2.12 (quintuplet, J=7.6 Hz, 2H), 2.75 (t, J=7.5 Hz, 2H), 2.89 (t, J=7.5 Hz, 2H), 3.83 (s, 3H), 6.53 (d, J=8.1 Hz, 1H), 7.66 (d, J=8.1 Hz, 1H). MS (ES+): 192 (M+H).

Workup

  1. customRemove the solvent under reduced pressure
  2. customPurify the residue by flash chromatography
  3. washeluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-fcf77f11ec60492194efe4ecf5395139
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

Loading…