Hydrochloric Acid → 4-Isopropoxycarbonylamino-indan-5-carboxylic acid methyl ester

HRID 2353936Notes

Reaction equation

HRID 2353936 reaction equation
Cl[C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3].[CH3:8][O:9][C:10]([C:12]1[C:13]([NH2:21])=[C:14]2[C:18](=[CH:19][CH:20]=1)[CH2:17][CH2:16][CH2:15]2)=[O:11].N1C=CC=CC=1.Cl>ClCCl>[CH3:8][O:9][C:10]([C:12]1[C:13]([NH:21][C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3])=[C:14]2[C:18](=[CH:19][CH:20]=1)[CH2:17][CH2:16][CH2:15]2)=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7917Isopropyl chloroformateHCID 593791394-Amino-indan-5-carboxylic acid methyl ester

Product 1

HCID 593791344-Isopropoxycarbonylamino-indan-5-carboxylic acid methyl esterYield 93.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add isopropyl chloroformate (2.22 mL, 2.22 mmol, 1.0 M in toluene) dropwise to a solution of 4-Amino-indan-5-carboxylic acid methyl ester (425 mg, 2.22 mmol) and pyridine (0.44 mL, 5.5 mmol) in dichloromethane (4.4 mL) at 0° C. under an atmosphere of nitrogen and stir at room temperature for 24 h. Add 1M HCl and separate the layers. Extract the aqueous layer with dichloromethane. Dry the organic layers over anhydrous sodium sulfate, filter, and remove the solvent under reduced pressure, to afford the title compound (576 mg, 93%): 1H NMR (MeOD) δ 1.37 (d, J=6.5 Hz, 6H), 2.16 (quintuplet, J=7.7 Hz, 2H), 2.97 (t, J=7.3 Hz, 2H), 3.05 (t, J=7.3 Hz, 2H), 3.94 (s, 3H), 4.97 (m, 1H), 7.22 (d, J=8.1 Hz, 1H), 7.80 (d, J=8.1 Hz, 1H). MS (ES+): 278 (M+H).

Workup

  1. customseparate the layers
  2. extractionExtract the aqueous layer with dichloromethane
  3. dry with materialDry the organic layers over anhydrous sodium sulfate
  4. filtrationfilter
  5. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-f090a857643c408cad6a8c1f2448b5bb
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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