Bromoacetonitrile → HCID 67243918, compound

HRID 2239594Notes

Reaction equation

HRID 2239594 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-dec90a53fb1f4035bd9e5db7a397a4e5
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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