Tetrahydrofuran → HCID 67356085, compound

HRID 2092595Notes

Reaction equation

HRID 2092595 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[N:11]1[CH2:20][CH2:19][C:14]2([O:18][CH2:17][CH2:16][O:15]2)[CH2:13][CH2:12]1.C1COCC1>[Pd].CO>[O:15]1[C:14]2([CH2:19][CH2:20][N:11]([C:3]3[CH:4]=[C:5]([NH2:8])[CH:6]=[CH:7][C:2]=3[CH3:1])[CH2:12][CH2:13]2)[O:18][CH2:17][CH2:16]1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 66656688HCID 66656688, compound

Product 1

HCID 67356085HCID 67356085, compoundYield 123%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 8-(2-Methyl-5-nitro-phenyl)-1,4-dioxa-8-aza-spiro[4.5]decane (100 mg, 0.278 mmol) in the mixed solvent of THF (3 ml) and methanol (3 ml) was added 10% Pd/C, and the reaction mixture was stirred for 12 hours at room temperature under a hydrogen balloon. The reaction mixture is filtered and the filtrate was concentrated under vacuum to give 3-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-4-methyl-phenylamine [29] (Yield: 84.9 mg, 95.2%) as a off white solid.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-ed07785ffe0c4139868b3a3b2b43efee
Source dataset
uspto-grants-2013_05
Patent number
US08440679B2

Reaction notes

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