Potassium Carbonate → HCID 71116054, compound

HRID 1423851Notes

Reaction equation

HRID 1423851 reaction equation
[NH2:1][CH2:2][C:3]1([CH2:19][CH3:20])[CH2:18][CH2:17][CH2:16][C:5]2([O:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:6]2)[CH2:4]1.F[C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[N+:30]([O-:32])=[O:31])[C:25]#[N:26].C(=O)([O-])[O-].[K+].[K+]>CC#N>[CH2:19]([C:3]1([CH2:2][NH:1][C:28]2[CH:27]=[C:24]([CH:23]=[CH:22][C:29]=2[N+:30]([O-:32])=[O:31])[C:25]#[N:26])[CH2:18][CH2:17][CH2:16][C:5]2([O:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([CH3:14])([CH3:15])[CH3:13])[CH2:6]2)[CH2:4]1)[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27833993-Fluoro-4-nitrobenzonitrileHCID 71116057HCID 71116057, compound

Product 1

HCID 71116054HCID 71116054, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a yellow solution containing 7-(aminomethyl)-7-ethyl-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-one (0.195 g, 0.690 mmol) and 3-fluoro-4-nitrobenzonitrile (0.126 g, 0.760 mmol) in MeCN (6.90 ml) was added potassium carbonate (0.191 g, 1.381 mmol). The reaction was stirred at rt for 16 h. The reaction was filtered through a frit, and the filtrate was concentrated onto florisil for purification on a 12 g silica gel column (5-25% EtOAc/hexanes, 30 min gradient; 25-55% EtOAc/hexanes, 5 min gradient; 30 mL/min elution; 254 nm detection) to afford the title compound (0.232 g, 75% yield) as an orange solid. MS (m/z) 429.2 (M+H+).

Workup

  1. filtrationThe reaction was filtered through a frit
  2. concentrationthe filtrate was concentrated onto florisil for purification on a 12 g silica gel column (5-25% EtOAc/hexanes, 30 min gradient; 25-55% EtOAc/hexanes, 5 min gradient; 30 mL/min elution; 254 nm detection)

Sources & evidence

ORD record
ord-ccb4959aefbb49ee9bab46442e26e2ab
Source dataset
uspto-grants-2015_01
Patent number
US08927585B2

Reaction notes

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