Hydrochloric Acid → HCID 58551183, compound

HRID 1908008Notes

Reaction equation

HRID 1908008 reaction equation
C(O[CH:4](OCC)[CH:5]1[C:14]2([CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[O:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=O)C.[NH2:31][NH2:32].Cl>CCO>[N:17]1([C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[CH2:16][CH2:15][C:14]2([C:5]3[CH:4]=[N:32][NH:31][C:6]=3[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[O:13]2)[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 58550808HCID 58550808, compound

Product 1

HCID 58551183HCID 58551183, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To tert-butyl 3-(diethoxymethyl)-4-oxo-spiro[chromane-2,4′-piperidine]-1′-carboxylate (15.1 g, 35.9 mmol) and hydrazine (1.35 mL, 43.1 mmol) in EtOH (120 mL) was added hydrochloric acid (900 μL of 4.0 M in dioxanes, 3.6 mmol). The mixture was heated at 60° C. for 2 h before it was cooled and the solvent was evaporated. The residue was purified by silica gel chromatography eluting with 0-100% ethyl acetate in hexanes to give tert-butyl spiro[1H-chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-carboxylate (8.76 g, 71%). ESI-MS m/z calc. 341.2. found 342.3 (M+1)+; Retention time: 1.69 minutes (3 min run).

Workup

  1. temperaturewas cooled
  2. customthe solvent was evaporated
  3. customThe residue was purified by silica gel chromatography
  4. washeluting with 0-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b82ffbcf76174107830c6dbb4fc69602
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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