Tetrahydrofuran → HCID 71247014, compound

HRID 715069Notes

Reaction equation

HRID 715069 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([N:23]2C(=O)C3C(=CC=CC=3)C2=O)[C:10]2([F:22])[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]2)[CH:5]=[CH:6][C:7]=1[F:8].C1COCC1.O.NN>CO>[NH2:23][CH:9]([C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=1)[C:10]1([F:22])[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 71247588HCID 71247588, compound

Product 1

HCID 71247014HCID 71247014, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 79 (238.5 mg, 0.500 mmol) and THF:MeOH (5.0 mL 1:1) was added hydrazine monohydrate (242.6 μL, 5.001 mmol) and the solution was heated to 60° C. for 16 h. The reaction was then cooled to RT and concentrated in vacuo. The residue was diluted with EtOAc and washed sequentially with water (1×), NaHCO3 (1×), and brine (1×), dried (Na2SO4), filtered and concentrated in vacuo to afford 160.1 mg (92.3%) of tert-butyl 3-(amino(3-chloro-4-fluorophenyl)methyl)-3-fluoropyrrolidine-1-carboxylate (78).

Workup

  1. temperatureThe reaction was then cooled to RT
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with EtOAc
  4. washwashed sequentially with water (1×), NaHCO3 (1×), and brine (1×)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-340c10b92cf543b486e8cea8f9bae3b4
Source dataset
uspto-grants-2015_11
Patent number
US09187462B2

Reaction notes

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