Ethyl orthoformate → HCID 67517270, compound

HRID 1466083Notes

Reaction equation

HRID 1466083 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([C:11]([OH:13])=[O:12])[CH2:6][CH2:5]2.[N-:14]=[N+:15]=[N-:16].[Na+].[CH:18](OCC)(OCC)OCC>C(O)(=O)C>[N:1]1([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[CH:7]([C:11]([OH:13])=[O:12])[CH2:6][CH2:5]3)[CH:18]=[N:16][N:15]=[N:14]1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 123184935-Amino-2,3-dihydro-1H-indene-1-carboxylic acid

Product 1

HCID 67517270HCID 67517270, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 5-aminoindane-1-carboxylic acid (2.95 g, 16.7 mmol), sodium azide (1.20 g, 18.3 mmol) and triethyl orthoformate (7.42 g, 50.1 mmol) in 20 mL of acetic acid was heated to 100° C. for 3 hrs. After the reaction was completed, the mixture was cooled to ambient temperature. The solution was removed under vacuum and the residue was diluted with EtOAc, washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified via silica gel column chromatography to give the crude product, which was re-crystallized from DCM to yield 5-(1H-tetrazol-1-yl)indane-1-carboxylic acid. 1H-NMR (400 MHz, DMSO) δ ppm 10.0 (s, 1H), 7.75 (s, 1H), 7.66-7.69 (m, 1H), 7.55 (d, J=8.1 Hz, 1H), 4.02-4.06 (m, 1H), 2.88-3.08 (m, 2H), 2.31 (q, J=8.1 Hz, 2H).

Workup

  1. customThe solution was removed under vacuum
  2. additionthe residue was diluted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified via silica gel column chromatography
  7. customto give the crude product, which
  8. customwas re-crystallized from DCM

Sources & evidence

ORD record
ord-c40d07e7eddd474fa349a83a6e507559
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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