Iodoethane → HCID 21912745, compound

HRID 1245599Notes

Reaction equation

HRID 1245599 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[NH:18][N:17]=[C:16]([O:19][CH3:20])[C:15]=2[CH3:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:24](I)[CH3:25]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:18]([CH2:24][CH3:25])[N:17]=[C:16]([O:19][CH3:20])[C:15]=2[CH3:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 21912816HCID 21912816, compound

Product 1

HCID 21912745HCID 21912745, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 30 mg (0.10 mmol) of 1-tert-butoxycarbonyl-4-(3-methoxy-4-methyl-(1H)-pyrazol-5-yl)piperidine (from Step D) in 1 mL of DMF at 0° C. was treated with 3.5 mg (0.15 mmol) of 95% NaH and 0.012 mL (0.15 mmol) of ethyliodide. After 50 minutes, the reaction was partitioned between 25 mL of EtOAc and 25 mL of brine. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by flash chromatography using 99:1 v/v CH2Cl2/acetone, 98:2 v/v CH2Cl2/acetone and 97:3 v/v CH2Cl2/acetone as the gradient to afford the title compound: RF: 0.39 (19:1 v/v CH2Cl2/acetone); 1H-NMR (500 MHz) δ 1.33 (t, J=7.1, 3H), 1.49 (s, 9H), 1.69–1.72 (m, 2H), 1.82–1.90 (m, 2H), 1.91 (s, 3H), 2.68–2.74 (m, 3H), 3.88 (s, 3H), 3.98 (q, J=7.1, 2H), 4.25 (m, 2H).

Workup

  1. customthe reaction was partitioned between 25 mL of EtOAc and 25 mL of brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e6aa4454da2942a3891904f17d7a93b3
Source dataset
uspto-grants-2006_10
Patent number
US07125887B2

Reaction notes

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