Hydrochloric Acid → HCID 178509356, compound

HRID 1297216Notes

Reaction equation

HRID 1297216 reaction equation
C([N:20]1[N:24]=[N:23][C:22]([C:25]2([C:33]#[N:34])[C:27]3([CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[CH2:26]2)=[N:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl>CO.C1COCC1.O=[Pt]=O>[NH:23]1[C:22]([C:25]2([CH2:33][NH2:34])[C:27]3([CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[CH2:26]2)=[N:21][N:20]=[N:24]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69516895HCID 69516895, compound

Product 1

HCID 178509356HCID 178509356, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of the 1-(2-trityl-2H-tetrazol-5-yl)-spiro[2.5]octane-1-carbonitrile (2.40 g, 2.39 mmol) in 100 mL MeOH:THF (1:1) was added PtO2 (0.15 g), concentrated HCl (1.67 g), and the mixture was hydrogenated in a Parr shaker at 48 psi for 20 h. The mixture was filtered and concentrated. Flash chromatography of the residue on silica gel (0.25:1.25:3.5 conc. NH4OH (aq):MeOH:CH2Cl2) furnished 0.40 g (36%) of C-[1-(1H-tetrazol-5-yl)-spiro[2.5]oct-1-yl]-methylamine as a colorless solid. 1H NMR (CD3OD) δ 3.77 (d, J=13.2 Hz, 1H, —CH2H2), 3.07 (d, J=13.2 Hz, 1H, —CH2H2), 1.66 (m, 1H), 1.53 (d, J=5.1 Hz, 1H, cyclopropyl —CHH), 1.47-1.59 (m, 4H), 1.22-1.42 (m, 3H), 1.06 (m, 1H), 0.97 (m, 1H), 0.88 (d, J=5.1 Hz, 1H, cyclopropyl —CHH). 13C NMR (CD3OD) δ 161.18, 31.61, 31.51, 26.00, 25.76, 25.30, 24.78, 21.67. LRMS: m/z 206.1 (M−1). Anal. Calc'd for C10H17N5: C, 57.95; H, 8.27; N, 33.79. Found: C, 56.83; H, 8.24; N, 33.40.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d250cfa628224cbf825da56a4c5fca26
Source dataset
uspto-grants-2007_07
Patent number
US07250433B2

Reaction notes

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