Sodium Hydroxide → HCID 57525626, compound

HRID 1594398Notes

Reaction equation

HRID 1594398 reaction equation
Cl.[C:2]([NH:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].[OH-].[Na+].[CH3:10][O:11][C:12]1([O:21][CH3:22])[CH2:15][CH:14]([C:16](=O)[CH2:17][C:18]#[N:19])[CH2:13]1>CCO>[C:2]([N:6]1[C:18]([NH2:19])=[CH:17][C:16]([CH:14]2[CH2:15][C:12]([O:11][CH3:10])([O:21][CH3:22])[CH2:13]2)=[N:7]1)([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 81889tert-Butylhydrazine monohydrochlorideHCID 575256253-(3,3-Dimethoxy-cyclobutyl)-3-oxo-propionitrile

Product 1

HCID 57525626HCID 57525626, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
75 °C

Procedure

To a slurry of tert-butylhydrazine hydrochloride (45.1 g, 362.0 mmol) in EtOH (1 L) was added NaOH pellets (12.4 g, 310.3 mmol). After 30 min, crude 3-(3,3-dimethoxy-cyclobutyl)-3-oxo-propionitrile in EtOH (300 mL) was added. The resulting slurry was heated to 75° C. (oil bath). After 14 hr, the reaction was cooled to room temperature, filtered, and concentrated under reduced pressure. Isopropyl ether was added to the resulting slurry. The slurry was stirred for 15 min, filtered, and concentrated to yield a viscous oil. Trituration with ether/hexanes (several crops) gave the title compound (56.2 g, 86% yield over two steps) as a colorless solid: mp 80.9° C. 500 MHz 1H NMR (CDCl3) d 5.50 (s, 1H), 3.51 (bs, 2H), 3.18 (s, 3H), 3.16 (s, 3H), 3.19-3.14 (m, 1H), 2.60-2.54 (m, 2H), 2.20-2.14 (m, 2H), 1.59 (s, 9H). LRMS m/z (APCI+) 254 (M+1).

Workup

  1. waitAfter 14 hr
  2. temperaturethe reaction was cooled to room temperature
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. additionIsopropyl ether was added to the resulting slurry
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a viscous oil

Sources & evidence

ORD record
ord-8fe61927dc7642568b2a8ae8f5eba017
Source dataset
uspto-grants-2007_11
Patent number
US07300944B2

Reaction notes

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