Ethyl orthoformate → HCID 67517270, compound

HRID 2173345Notes

Reaction equation

HRID 2173345 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 actic 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 with silica gel column chromatograph to give the crude product, then re-crystalization 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 with silica gel column chromatograph
  7. customto give the crude product
  8. customre-crystalization from DCM

Sources & evidence

ORD record
ord-337c63e64e2240abbbab462ab6d2463f
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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