benzyl spiro[1H-chromeno[4,3-c]pyrazole-4,4'-piperidine]-1'-carboxylate → 1H-spiro[chromeno[4,3-c]pyrazole-4,4'-piperidine]

HRID 1908016Notes

Reaction equation

HRID 1908016 reaction equation
[N:1]1(C(OCC2C=CC=CC=2)=O)[CH2:6][CH2:5][C:4]2([C:18]3[CH:17]=[N:16][NH:15][C:14]=3[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[O:7]2)[CH2:3][CH2:2]1>CO.[Pd]>[NH:1]1[CH2:6][CH2:5][C:4]2([C:18]3[CH:17]=[N:16][NH:15][C:14]=3[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[O:7]2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 58550771benzyl spiro[1H-chromeno[4,3-c]pyrazole-4,4'-piperidine]-1'-carboxylate

Product 1

HCID 585517941H-spiro[chromeno[4,3-c]pyrazole-4,4'-piperidine]Yield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl spiro[1H-chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-carboxylate (1.11 g, 2.96 mmol) and palladium (10% wt on carbon, 157 mg, 0.15 mmol) in MeOH (15 mL) was set under hydrogen (1 atm) and stirred vigorously at room temperature for 3 hours. The reaction mixture was filtered through Celite and the filtrate was concentrated to afford 1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine] (570 mg, 80%). ESI-MS m/z calc. 241.1. found 242.5 (M+1)+; Retention time: 0.42 minutes (3 min run).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-bd66f55436854f29bcfb0b9d567872c4
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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