Ethyl Acetate → 6-((Tert-butyldiphenylsilyloxy)methyl)-4-methylpyridin-3-amine

HRID 1811580Notes

Reaction equation

HRID 1811580 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[CH:25]=[C:24]([CH3:26])[C:23]([N+:27]([O-])=O)=[CH:22][N:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C>[NH4+].[Cl-].[Zn]>[Si:1]([O:18][CH2:19][C:20]1[N:21]=[CH:22][C:23]([NH2:27])=[C:24]([CH3:26])[CH:25]=1)([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 586715992-((Tert-butyldiphenylsilyloxy)methyl)-4-methyl-5-nitropyridine

Product 1

HCID 586715586-((Tert-butyldiphenylsilyloxy)methyl)-4-methylpyridin-3-amine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 2-((tert-butyldiphenylsilyloxy)methyl)-4-methyl-5-nitropyridine (1.5 g, 3.7 mmol) in 20 ml of sat. NH4Cl, were added zinc (1.7 g, 26 mmol) portionwise at 0° C. for 10 min. The reaction was stirred at the same temperature for 1 hr. The reaction was added with ethyl acetate (20 mL) and stirred for additional 1 hr. The organic layer was taken up, washed with H2O, and dried over MgSO4. The ethyl acetate was concentrated under vacuum to afford 6-((tert-butyldiphenylsilyloxy)methyl)-4-methylpyridin-3-amine in 72% (1.0 g). The compound was used for the next step without further purification. 1HNMR (CDCl3, 400 MHz) δ 1.10 (s, 9H), 2.21 (s, 3H), 4.64 (s, 2H), 5.01˜5.13 (b, 2H), 7.12 (s, 1H), 7.31˜7.71 (m, 10H), 7.89 (s, 1H). Exact mass calculated for C23H28N2OSi 376.57 found 377.4 (MH+).

Workup

  1. stirringstirred for additional 1 hr
  2. washwashed with H2O
  3. dry with materialdried over MgSO4
  4. concentrationThe ethyl acetate was concentrated under vacuum

Sources & evidence

ORD record
ord-06960e2346774681bcafcf40c4ce7826
Source dataset
uspto-grants-2013_01
Patent number
US08362248B2

Reaction notes

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