Hydrochloric Acid → HCID 66810300, compound

HRID 1477314Notes

Reaction equation

HRID 1477314 reaction equation
[CH2:1]=[C:2]1[CH2:7][O:6][C@H:5]([C:8]2[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:9]=2[F:16])[C@@H:4]([N+:17]([O-])=O)[CH2:3]1.Cl.CCOCC.[OH-].[Na+]>C(O)C.[Zn]>[CH2:1]=[C:2]1[CH2:7][O:6][C@H:5]([C:8]2[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:9]=2[F:16])[C@@H:4]([NH2:17])[CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 66810550HCID 66810550, compound

Product 1

HCID 66810300HCID 66810300, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

To a vigorously stirred suspension of (2R,3S)-5-methylene-3-nitro-2-(2,4,5-trifluorophenyl)tetrahydro-2H-pyran (200 mg, 0.73 mmol) and zinc powder (561 mg, 8.59 mmol) in ethanol (7 mL) was added 6N hydrochloric acid (2.3 mL, 14 mmol). After one hour, the mixture was treated with ether (100 mL) and aqueous sodium hydroxide solution (2.5N, 40 mL). The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and evaporated to yield (2R,3S)-5-methylene-2-(2,4,5-trifluorophenyl)tetrahydro-2H-pyran-3-amine which was used in the next step without further purification.

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-25d60d862ef7418494385c1d37f414a7
Source dataset
uspto-grants-2016_08
Patent number
US09403790B2

Reaction notes

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