Iodoethane → HCID 66864622, compound

HRID 1615822Notes

Reaction equation

HRID 1615822 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[N:10]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:5]=[C:6]([F:8])[CH:7]=1.I[CH2:24][CH3:25].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:36]1COC[CH2:37]1>>[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:11](=[O:15])[C:12]([CH2:24][CH3:25])([CH2:36][CH3:37])[CH2:13][CH2:14]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 4

HCID 6340IodoethaneHCID 8028Tetrahydrofuran2×HCID 2724254Sodium bis(trimethylsilyl)amideHCID 66865136HCID 66865136, compound

Product 1

HCID 66864622HCID 66864622, compound

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl (2S)-2-(3,5-difluorophenyl)-6-oxopiperidine-1-carboxylate from Step C (1.53 g, 4.91 mmol) and iodoethane (0.993 mL, 12.3 mmol) in THF (15 mL) at −78° C. was added a 1 M solution of sodium bis(trimethylsilyl)amide in THF (10.8 mL, 10.8 mmol) dropwise over 15 min. The resulting mixture was stirred at −78° C. for 10 min and at 0° C. for 2 h, then quenched with saturated aqueous NH4Cl (50 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 50:50, to give the title compound. MS: m/z=312 (M−C4H7).

Workup

  1. customquenched with saturated aqueous NH4Cl (50 mL)
  2. extractionextracted with EtOAc (3×50 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-55c38881836d470a977a649971c7ccc8
Source dataset
uspto-grants-2014_07
Patent number
US08765759B2

Reaction notes

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