tert-Butoxy bis(dimethylamino)methane → HCID 69849039, compound

HRID 1838309Notes

Reaction equation

HRID 1838309 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]([O:15][CH:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)[N:7]=1)[CH3:2].C(O[CH:29](N(C)C)[N:30]([CH3:32])[CH3:31])(C)(C)C>>[CH2:1]([O:3][C:4](=[O:23])[C:5]([C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]([O:15][CH:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)[N:7]=1)=[CH:29][N:30]([CH3:32])[CH3:31])[CH3:2]

Participants

3

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 60060150HCID 60060150, compound

Product 1

HCID 69849039HCID 69849039, compound

Conditions

Temperature
65 °C

Procedure

A mixture of [6-(1-methyl-piperidin-4-yloxy)-3-nitro-pyridin-2-yl]-acetic acid ethyl ester (5.93 g, 18.3 mmol) and tert-butoxybis(dimethylamino)methane (5.7 mL, 27.5 mmol) at is heated 65° C. for a period of 6 h. The mixture is cooled to room temperature and purified by flash chromatography on silica (gradient elution with 4% MeOH/CHCl3 with 0.1% NH4OH to 6% MeOH/CHCl3 with 0.1% NH4OH) to give the title compound as a dark orange oil: 1H NMR (400 MHz, CDCl3) δ 8.03 (d, 1H, J=9.1 Hz), 7.5 (s, 1H), 6.49 (d, 1H, J=9.1 Hz), 5.00-4.96 (m, 1H), 3.97-3.82 (m, 2H), 2.69 (br s, 6H), 2.60-2.50 (m, 2H), 2.20-2.10 (m, 2H), 2.16 (s, 3H), 1.92-1.85 (m, 2H), 1.74-1.65 (m, 2H), 0.98 (t, 3H, J=7.1 Hz); 13C NMR (100 MHz, CDCl3) δ 167.7, 163.3, 151.7, 150.8, 141.8, 135.5, 109.3, 96.8, 71.7, 59.8, 52.9, 46.3, 43.6, 31.4, 30.9, 14.4; MS (CI) m/z 379.3 (M+1).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. custompurified by flash chromatography on silica (gradient elution with 4% MeOH/CHCl3 with 0.1% NH4OH to 6% MeOH/CHCl3 with 0.1% NH4OH)

Sources & evidence

ORD record
ord-ac617ad4cb4e4494af52e38c001f996a
Source dataset
uspto-grants-2004_01
Patent number
US06673811B1

Reaction notes

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