Trimethylsilyl iodide → 4-(4-Amino-4-methyl-piperidine-1-carbonyl)-benzoic acid methyl ester

HRID 855834Notes

Reaction equation

HRID 855834 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:17][CH2:16][C:15]([NH:19]C(OCC3C=CC=CC=3)=O)([CH3:18])[CH2:14][CH2:13]2)=[O:11])=[CH:6][CH:5]=1.I[Si](C)(C)C>C(#N)C>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:5]=[CH:6][C:7]([C:10]([N:12]2[CH2:13][CH2:14][C:15]([NH2:19])([CH3:18])[CH2:16][CH2:17]2)=[O:11])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 667570404-(4-Benzyloxycarbonylamino-4-methyl-piperidine-1-carbonyl)benzoic Acid Methyl Ester

Product 1

HCID 667569774-(4-Amino-4-methyl-piperidine-1-carbonyl)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of Example 32A (0.2 g, 0.49 mmol) in acetonitrile (4.0 mL) at room temperature was added iodotrimethysilane (0.11 mL, 0.75 mmol). The reaction mixture was stirred at 50° C. for 30 minutes and then concentrated under reduced pressure. The solid residue was washed with acetone and ether and filtered to provide titled compound. MS (CI) m/z 277(M+1)+; 1H NMR (300 MHz, DMSO-d6) δ ppm 8.04(d, 2H), 7.90 (bs, 2H NH2-DMSO solvent), 7.50(d, 2H), 3.88 (s, 3H), 3.35-3.20 (m, 4H), 1.79-1.58 (m, 4H), 1.35 (s, 3H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. washThe solid residue was washed with acetone and ether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-bd389a45d9334a7390064c0d87a0141a
Source dataset
uspto-grants-2007_08
Patent number
US07262207B2

Reaction notes

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