Hydrazine hydrate (1:1) → methyl 7,7-dimethyl-1-oxo-2,3,4,6,7,8-hexahydro-1H-pyrido[3,4-b]pyrrolizine-9-carboxylate

HRID 520308Notes

Reaction equation

HRID 520308 reaction equation
[O:1]=[C:2]1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][C:14]1[N:15]2[C:19](=[C:20]([C:26]([O:28][CH3:29])=[O:27])[C:21]=1C(OC)=O)[CH2:18][C:17]([CH3:31])([CH3:30])[CH2:16]2.O.NN>CCO>[CH3:31][C:17]1([CH3:30])[CH2:18][C:19]2[N:15]([C:14]3[CH2:13][CH2:12][NH:3][C:2](=[O:1])[C:21]=3[C:20]=2[C:26]([O:28][CH3:29])=[O:27])[CH2:16]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 117777472dimethyl 5-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-2,2-dimethyl-2,3-dihydro-1H-pyrrolizine-6,7-dicarboxylate

Product 1

HCID 117777383methyl 7,7-dimethyl-1-oxo-2,3,4,6,7,8-hexahydro-1H-pyrido[3,4-b]pyrrolizine-9-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 137k (15.0 g, 35.4 mmol) in EtOH (100 mL) was added hydrazine hydrate (3.5 g, 70.8 mmol). See FIG. 2. The mixture was stirred at 90° C. for 2 h. After cooling the reaction to RT, the resultant precipitate was filtered and washed with ethanol. The filtrate was concentrated to give crude methyl 7,7-dimethyl-1-oxo-2,3,4,6,7,8-hexahydro-1H-pyrido[3,4-b]pyrrolizine-9-carboxylate 137l as a yellow solid.

Workup

  1. temperatureAfter cooling
  2. customthe reaction to RT
  3. filtrationthe resultant precipitate was filtered
  4. washwashed with ethanol
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3467facd1d4848b98500afe25c334c84
Source dataset
uspto-grants-2016_05
Patent number
US09326985B2

Reaction notes

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