Bromoacetonitrile → HCID 67243918, compound

HRID 2421997Notes

Reaction equation

HRID 2421997 reaction equation
[H-].[Na+].[OH:3][CH:4]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5]1.Br[CH2:16][C:17]#[N:18]>C1COCC1>[C:17]([CH2:16][O:3][CH:4]1[CH2:5][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7]1)#[N:18]

Participants

5

Reactant 3

HCID 11534Bromoacetonitrile3×HCID 24758Sodium hydride2×HCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylate

Product 1

HCID 67243918HCID 67243918, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (60% dispersion in mineral oil, 276 mg, 6.89 mmol) was added to an ice cold solution of tert-butyl 3-hydroxyazetidine-1-carboxylate (0.92 mg, 5.30 mmol) in THF (8 mL) and stirred for 15 mins. Bromoacetonitrile (0.52 mL, 7.43 mmol) was added dropwise and the reaction mixture allowed to warm to room temperature. After 2.5 h, bromoacetonitrile (0.074 mL, 1.06 mmol) was added and the reaction mixture stirred at rt. After 17 h, NaH (60% dispersion in mineral oil, 0.085 mg, 2.12 mmol) and bromoacetonitrile (0.074 mL, 1.06 mmol) were added. After 2 h the reaction mixture was evaporated to dryness and the crude product purified on a Biotage Horizon HPFC system eluting with 5-90% EtOAc in petroleum ether (40-60° C.) to give the title compound (0.47 g, 42%) as an oil. 1H NMR (CDCl3): δ 4.46-4.40 (m, 1H), 4.24 (s, 2H), 4.17 (dd, 2H), 3.92 (dd, 2H), 1.45 (s, 9H); 13C NMR (CDCl3): δ 156.3, 115.6, 80.2, 69.3, 56.3, 54.6, 28.6.

Workup

  1. waitAfter 2.5 h
  2. stirringthe reaction mixture stirred at rt
  3. waitAfter 17 h
  4. customAfter 2 h the reaction mixture was evaporated to dryness
  5. customthe crude product purified on a Biotage Horizon HPFC system
  6. washeluting with 5-90% EtOAc in petroleum ether (40-60° C.)

Sources & evidence

ORD record
ord-eb4ca9f37b9e4a87bfb3ec477a5332f1
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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