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

HRID 2204113Notes

Reaction equation

HRID 2204113 reaction equation
[CH2:1]([N:3]1[C:7]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[O:14][C:15]3([CH2:20][CH2:19][N:18](C(OCC4C=CC=CC=4)=O)[CH2:17][CH2:16]3)[C:6]=2[CH:5]=[N:4]1)[CH3:2].[H][H]>CO.[Pd]>[CH2:1]([N:3]1[C:7]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[O:14][C:15]3([CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[C:6]=2[CH:5]=[N:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 58551072benzyl 1-ethyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4'-piperidine]-1'-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 585507281-ethyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4'-piperidine]Yield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl 1-ethyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-carboxylate (530 mg, 1.3 mmol) was stirred in methanol (9.5 mL) with Pd/C (70 mg, 0.070 mmol) under a balloon of hydrogen for 16 h. The reaction was filtered through a syringe filter and the solvent evaporated to give 1-ethyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine] (350 mg, 99%). ESI-MS m/z calc. 269.2, found 270.5 (M+1)+; Retention time: 0.80 minutes (3 min run).

Workup

  1. filtrationThe reaction was filtered through a syringe
  2. filtrationfilter
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-2aa1cafaf14042f39af06aec21535003
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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