Trimethylsilyl cyanide → HCID 86620141, compound

HRID 1664920Notes

Reaction equation

HRID 1664920 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]1[CH2:15][NH:14][C:13](=O)[C@H:12]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:11][CH2:10]1.C[Si](C)(C)[C:27]#[N:28].C(=O)(O)[O-].[Na+]>O1CCCC1.[H-].[Cl-].[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Zr+2]>[C:27]([CH:13]1[C@H:12]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:11][CH2:10][C@@H:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[F:1])[CH2:15][NH:14]1)#[N:28]

Participants

6

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 516892Sodium BicarbonateHCID 23657400tert-Butyl [(3R,6S)-6-(2,3-difluorophenyl)-2-oxoazepan-3-yl]carbamate

Product 1

HCID 86620141HCID 86620141, compound

Reagents, catalysts & solvents 2

HCID 131718033Bis(cyclopenta-1,3-diene);hydride;zirconium(2+);chlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tert-butyl [(3R,6S)-6-(2,3-difluorophenyl)-2-oxoazepan-3-yl]carbamate (0.67 g, 1.97 mmol) in tetrahydrofuran (10 mL) was slowly added to a solution of zirconocene chloride hydride (0.76 g, 2.95 mmol) in tetrahydrofuran (5.0 mL) at −20° C. After 15 min, the mixture was allowed to warm to ambient temperature. After 3 h, trimethylsilanecarbonitrile (1.31 mL, 9.84 mmol) was added. After 16 h, saturated aqueous sodium bicarbonate was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts were washed with Rochelle's salt (1.0 M in water), brine, dried over sodium sulfate, filtered, and concentrated. MS 352.1 (M+1).

Workup

  1. waitAfter 3 h
  2. waitAfter 16 h
  3. extractionthe mixture was extracted with dichloromethane (3×)
  4. washThe combined organic extracts were washed with Rochelle's salt (1.0 M in water), brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ffdce246bc8247b0a2c7538002034eaa
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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