Water → HCID 22993466, compound

HRID 1275243Notes

Reaction equation

HRID 1275243 reaction equation
C([O:5][C:6](=[O:22])[NH:7][CH:8]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=1)[C:9]1(O)[CH2:12][CH2:11][CH2:10]1)(C)(C)C.[H-].[Na+].O>C1COCC1>[F:21][C:16]1[CH:15]=[C:14]([CH:8]2[C:9]3([CH2:10][CH2:11][CH2:12]3)[O:22][C:6](=[O:5])[NH:7]2)[CH:19]=[CH:18][C:17]=1[F:20]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 22993450HCID 22993450, compound

Product 1

HCID 22993466HCID 22993466, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

To a well stirred solution of [(3,4-difluorophenyl)-(1-hydroxy-cyclobutyl)-methyl]-carbamic acid-tert-butyl ester (1.0 g, 3.2 mmol) in THF (20 mL) was added 95% NaH (0.2 g, 8.3 mmol) at room temperature. The resulting suspension was stirred for 3 h at about 35° C. (warm water bath) and then quenched carefully with ice. The biphasic mixture was extracted with 100 mL of EtOAc, washed with brine, dried over Na2SO4, filtered and the solvent was removed in vacuo to yield 8-(3,4-difluorophenyl)-5-oxa-7-aza-spiro[3.4]octan-6-one in racemic form as a white solid.

Workup

  1. customquenched carefully with ice
  2. extractionThe biphasic mixture was extracted with 100 mL of EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-13fda9e1aa1044f9b04b6541f6cb09c1
Source dataset
uspto-grants-2000_12
Patent number
US06159990

Reaction notes

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