Water → HCID 57504576, compound

HRID 1098084Notes

Reaction equation

HRID 1098084 reaction equation
[Li]CCCC.[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][N:8]=1.[Si:14]([O:21][C@@H:22]([CH2:28][CH2:29][N:30]([CH3:32])[CH3:31])[C:23](OCC)=[O:24])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].O>C1COCC1.CCOC(C)=O>[Si:14]([O:21][C@@H:22]([CH2:28][CH2:29][N:30]([CH3:32])[CH3:31])[C:23]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][N:8]=1)=[O:24])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 153482-Amino-5-methylpyridineHCID 57504575HCID 57504575, compoundHCID 178418339Butyllithium

Product 1

HCID 57504576HCID 57504576, compoundYield 17.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

n-BuLi (3.40 mL, 1.6 M in hexanes, 5.44 mmol) was added slowly to a stirred solution of 2-amino-5-picoline (616 mg, 5.70 mmol) in anhydrous THF (8 mL). The reaction mixture was kept at ambient temperature for 10 minutes before a solution of ethyl (2S)-2-{[tert-butyl(dimethyl)silyl]oxy}-4-(dimethylamino)butanoate (Step 2) (1.50 g, 5.18 mmol) in anhydrous THF (2 mL) was added. The reaction mixture was stirred at ambient temperature for 1 h. Water and EtOAc were added and the two phases were separated. The aqueous phase was extracted with EtOAc. The organic extracts were combined and washed with water, dried over MgSO4 and concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with EtOAc) to give the title compound (320 mg), 1H NMR (300 MHz, CDCl3) δ 8.89 (br s, 1H), 8.12 (m, 2H), 7.51 (dd, 1H), 4.32 (t, 1H), 2.47 (m, 1H), 2.31 (m, 4H), 2.21 (s, 6H), 1.97 (m, 2H), 0.98 (s, 9H), 0.15 (d, 6H).

Workup

  1. additionwas added
  2. customthe two phases were separated
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified with column chromatography (silica gel, eluting with EtOAc)

Sources & evidence

ORD record
ord-64935ff487f74c5b8c2d33167401514d
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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