Sodium Hydroxide → 7-Amino-5-benzyl-7-methyl-5-azaspiro[2.4]heptane

HRID 389249Notes

Reaction equation

[H-].COCCO[Al+]OCCOC.[Na+].[H-].[NH2:15][C:16]1([CH3:31])[C:20]2([CH2:22][CH2:21]2)[C:19](=O)[N:18]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:17]1.[OH-].[Na+]>C1(C)C=CC=CC=1>[NH2:15][C:16]1([CH3:31])[C:20]2([CH2:22][CH2:21]2)[CH2:19][N:18]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:17]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution (65% toluene solution) of sodium bis(2-methoxyethoxy)aluminum hydride (1.65 kg, 3.5 eq.) in toluene (870 mL) was added to a solution of 7-amino-5-benzyl-4-oxo-7-methyl-5-azaspiro[2.4]heptane (348 g, 1.51 mmol) in toluene (2.62 L), and the mixture was stirred at an internal temperature of 60° C. for 1 hour. The reaction mixture was cooled with ice. Aqueous sodium hydroxide solution (5N) was added to the cooled mixture, and the aqueous layer was extracted with toluene. The thus-obtained organic layers were combined, and the solvent of the combined organic layer was evaporated under reduced pressure, to thereby yield the title product as brown oil (343 g, purity: 81.3%, yield: 100%).

Workup

temperatureThe reaction mixture was cooled with ice
extractionthe aqueous layer was extracted with toluene
customthe solvent of the combined organic layer was evaporated under reduced pressure

Sources & evidence

ORD record: ord-8e9cf16a956447b1966624755e04305c
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08378119B2

Reaction notes

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