Hydrazine hydrate (1:1) → (2R)-tert-butyl 2-(2-amino-2-(3-chloro-4-fluorophenyl)ethyl)pyrrolidine-1-carboxylate

HRID 2279590Notes

Reaction equation

HRID 2279590 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([N:23]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:10][C@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:5]=[CH:6][C:7]=1[F:8].O.NN>C1COCC1.CO>[NH2:23][CH:9]([C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=1)[CH2:10][C@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86705572(2R)-tert-butyl 2-(2-(3-chloro-4-fluorophenyl)-2-(1,3-dioxoisoindolin-2-yl)ethyl)pyrrolidine-1-carboxylate

Product 1

HCID 86705573(2R)-tert-butyl 2-(2-amino-2-(3-chloro-4-fluorophenyl)ethyl)pyrrolidine-1-carboxylateYield 58.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 303 (0.0507 g, 0.1072 mmol) and THF/MeOH (1:1) was added hydrazine monohydrate (0.080 mL, 1.072 mmol) and the reaction stirred at RT 3 d. A thick white precipitate formed which was filtered through CELITE. The solution was concentrated and purified by SiO2 chromatography to afford 0.0214 g (58%) of (2R)-tert-butyl 2-(2-amino-2-(3-chloro-4-fluorophenyl)ethyl)pyrrolidine-1-carboxylate (305) as a clear oil.

Workup

  1. customA thick white precipitate formed which
  2. filtrationwas filtered through CELITE
  3. concentrationThe solution was concentrated
  4. custompurified by SiO2 chromatography

Sources & evidence

ORD record
ord-848ceeb7810247c298e858ac557ac3a6
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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