Lithium hydroxide, monohydrate → HCID 76831113, compound

HRID 1186167Notes

Reaction equation

HRID 1186167 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([C:8]23[CH2:14][CH:13]2[CH2:12][O:11]C(=O)[NH:9]3)[CH:7]=1.O.[OH-].[Li+]>C(O)C.O.[Cl-].[Na+].O>[NH2:9][C:8]1([C:6]2[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[F:16])[CH2:14][CH:13]1[CH2:12][OH:11]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 76831213HCID 76831213, compound

Product 1

HCID 76831113HCID 76831113, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (1SR,6RS)-1-(5-bromo-2-fluoro-phenyl)-4-oxa-2-aza-bicyclo[4.1.0]heptan-3-one (intermediate B7A) (1.48 g, 5.17 mmol) and lithium hydroxide monohydrate (LiOH.H2O) (2.17 g, 52 mmol) in ethanol (EtOH) (2.5 ml) and water (12.5 ml) was stirred at 100° C. for 16 h. Poured into ice water, added brine, extracted twice with tert-butyl methyl ether (TBME), washed organic layer with brine, dried over sodium sulfate. Removal of the solvent in vacuum left the title compound as a light brown oil (1.224 g, 91%), which was used without further purification. MS (ISP): m/z=242.2 [(M−NH2)+] and 244.2 [(M+2−NH2)+].

Workup

  1. extractionextracted twice with tert-butyl methyl ether (TBME)
  2. washwashed organic layer with brine
  3. dry with materialdried over sodium sulfate
  4. customRemoval of the solvent in vacuum
  5. waitleft the title compound as a light brown oil (1.224 g, 91%), which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-3444bebe6d404a6f963c5f8703ce262d
Source dataset
uspto-grants-2014_03
Patent number
US08673894B2

Reaction notes

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