Sodium Hydroxide → 5-Benzyl-7-t-butoxycarbonylamino-7-methyl-5-azaspiro[2.4]heptane

HRID 389254Notes

Reaction equation

HRID 389254 reaction equation
[NH2:1][C:2]1([CH3:16])[C:6]2([CH2:8][CH2:7]2)[CH2:5][N:4]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:3]1.[C:17](OC([O-])=O)([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:9]([N:4]1[CH2:3][C:2]([NH:1][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])([CH3:16])[C:6]2([CH2:8][CH2:7]2)[CH2:5]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 22064466Tert-butyldicarbonateHCID 249623127-Amino-5-benzyl-7-methyl-5-azaspiro[2.4]heptane

Product 1

HCID 577586395-Benzyl-7-t-butoxycarbonylamino-7-methyl-5-azaspiro[2.4]heptaneYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

7-Amino-5-benzyl-7-methyl-5-azaspiro[2.4]heptane (7.3 g) was dissolved in toluene (30 mL). t-Butyl dicarbonate (9.3 mL) and 1N aqueous sodium hydroxide (10 mL) were added to the solution, followed by stirring for 15 hours at room temperature and then for 4 hours at 50° C. After completion of reaction, the toluene layer was separated and washed with water, followed by drying with sodium sulfate. The desiccant was removed through filtration, and the filtrate was concentrated under reduced pressure. The residue was purified through silica gel chromatography (hexane:ethyl acetate), to thereby yield the title product (8.745 g, yield: 82%). Notably, when optically active 7-amino-5-benzyl-7-methyl-5-azaspiro[2.4]heptane is treated in accordance with the above-described procedure, the corresponding optically active target product can be yielded without decreasing optical purity.

Workup

  1. waitfor 4 hours at 50° C
  2. customAfter completion of reaction
  3. customthe toluene layer was separated
  4. washwashed with water
  5. dry with materialby drying with sodium sulfate
  6. customThe desiccant was removed through filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified through silica gel chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-98ceb8c0a23b46059a5042a24b714266
Source dataset
uspto-grants-2013_02
Patent number
US08378119B2

Reaction notes

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