Sodium hydride → HCID 86616772, compound

HRID 1725605Notes

Reaction equation

HRID 1725605 reaction equation
[H-].[Na+].[O:3]=[C:4]1[C@@H:10]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:9][CH2:8][CH2:7][C@@H:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[NH:5]1.[CH:25]1([CH2:28]Br)[CH2:27][CH2:26]1>CN(C)C=O>[CH:25]1([CH2:28][N:5]2[C@H:6]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:7][CH2:8][CH2:9][C@H:10]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:4]2=[O:3])[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 86616770HCID 86616770, compound

Product 1

HCID 86616772HCID 86616772, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil; 20.6 mg, 0.52 mmol) was added to a solution of tert-butyl (3S,7S)-2-oxo-7-phenylazepan-3-ylcarbamate (143 mg, 0.47 mmol) and cyclopropylmethyl bromide (0.11 mL, 1.18 mmol) in N,N-dimethylformamide (1 mL) at 0 □C, and the mixture was allowed to warm to ambient temperature. After 14 h, the reaction was quenched with water and the mixture was extracted with ethyl acetate. The organic layer was washed with water (3×), saturated brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (10% ethyl acetate/hexanes→30% ethyl acetate/hexanes) gave the title compound (144 mg). MS 359 (M+1).

Workup

  1. customthe reaction was quenched with water
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water (3×), saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (10% ethyl acetate/hexanes→30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-fad744ef7acc45f6885710041f76ef38
Source dataset
uspto-grants-2009_02
Patent number
US07491713B2

Reaction notes

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