Water → tert-Butyl 3-fluoro-4-oxoazepane-1-carboxylate

HRID 876418Notes

Reaction equation

HRID 876418 reaction equation
[F:1][CH:2]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][CH2:5][CH:4](C(OCC)=O)[C:3]1=[O:21].O.[Li+].[Cl-]>CS(C)=O>[F:1][CH:2]1[C:3](=[O:21])[CH2:4][CH2:5][CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8]1

Participants

5

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 67230662644982-11-6

Product 1

HCID 53415294tert-Butyl 3-fluoro-4-oxoazepane-1-carboxylateYield 21%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
125 °C

Procedure

The product from Step A was dissolved in DMSO (200 mL) and H2O (8.29 g, 460 mmol) followed by addition of LiCl (19.5 g, 460 mmol). The solution was warmed to 125° C. and the mixture was stirred overnight. The mixture was cooled to ambient temperature and partitioned between EtOAc (2.5 L) and water:brine (1:1, 2.0 L). The mixture was filtered through activated charcoal over Celite, which was washed with EtOAc, forming visible layers. The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (10 to 80% EtOAc/hexanes) providing 4.5 g (21%) of the product as a thick pale orange oil.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. custompartitioned between EtOAc (2.5 L) and water:brine (1:1, 2.0 L)
  3. filtrationThe mixture was filtered through activated charcoal over Celite, which
  4. washwas washed with EtOAc
  5. customforming visible layers
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography (10 to 80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f927669aee73420db3c90821f3d43d22
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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