Sodium hydride → HCID 91618405, compound

HRID 595256Notes

Reaction equation

HRID 595256 reaction equation
[H-].[Na+].O[CH:4]([C:7]1([NH:10][C:11](=[O:17])[O:12]C(C)(C)C)[CH2:9][CH2:8]1)[CH2:5][OH:6]>C1COCC1>[OH:6][CH2:5][CH:4]1[C:7]2([CH2:8][CH2:9]2)[NH:10][C:11](=[O:12])[O:17]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 131734578HCID 131734578, compound

Product 1

HCID 91618405HCID 91618405, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

Sodium hydride (197 mg, 4.92 mmol) was added to a solution of tert-butyl [1-(1,2-dihydroxyethyl)cyclopropyl]carbamate (100 mg, 0.46 mmol) in THF (1 mL) at room temperature. The mixture was stirred at 30° C. under a nitrogen atmosphere for 16 hours. After being cooled to 20° C., the mixture was diluted with ice water (1 mL) and then extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (methanol/dichloromethane) to give 7-(hydroxymethyl)-6-oxa-4-azaspiro[2.4]heptan-5-one. 1H NMR (300 MHz, DMSO-d6): δ 7.62 (br s, 1H), 5.00-4.96 (m, 1H), 4.40-4.35 (m, 1H), 3.51-3.40 (m, 2H), 1.01-0.88 (m, 1H), 0.80-0.55 (m, 3H).

Workup

  1. temperatureAfter being cooled to 20° C.
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on silica gel (methanol/dichloromethane)

Sources & evidence

ORD record
ord-f829c5f62b314cbd949c72fd0e49324a
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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