Sodium hydride → Tert-butyl 3-oxa-7-azabicyclo[4.1.0]heptane-7-carboxylate

HRID 39418Notes

Reaction equation

HRID 39418 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[C@H:13](Br)[CH2:12][CH2:11][O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+]>CN(C)C=O>[C:1]([O:5][C:6]([N:7]1[CH:8]2[CH:13]1[CH2:12][CH2:11][O:10][CH2:9]2)=[O:15])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 67360126trans-(4-Bromo-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester2×

Product 1

HCID 58381262Tert-butyl 3-oxa-7-azabicyclo[4.1.0]heptane-7-carboxylateYield 71.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

trans-(4-Bromo-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester (intermediate D) (1.0 g, 3.5 mmol) was dissolved in 35 mL dimethylformamide. Sodium hydride (60%, 214 mg, 5.4 mmol) was added at 0° O. The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was quenched by careful addition of water. The mixture was extracted three times with diethylether. The combined organic phases were dried on sodium sulfate, filtered and evaporated. Purification of the residue by flash chromatography on silica gel (heptane/ethyl acetate 1:0→1:1) yielded the title compound as a colorless oil (499 mg, 70%), MS: m/e=143 [(M-buten)+].

Workup

  1. customThe reaction mixture was quenched by careful addition of water
  2. extractionThe mixture was extracted three times with diethylether
  3. customThe combined organic phases were dried on sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customPurification of the residue by flash chromatography on silica gel (heptane/ethyl acetate 1:0→1:1)

Sources & evidence

ORD record
ord-c77f49ecc74c4ba682332e68a4aeb914
Source dataset
uspto-grants-2013_09
Patent number
US08524909B2

Reaction notes

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