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

HRID 389252Notes

Reaction equation

HRID 389252 reaction equation
C(O)(=O)[C@@H](C1C=CC=CC=1)O.[NH2:12][C:13]1([CH3:27])[C:17]2([CH2:19][CH2:18]2)[CH2:16][N:15]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:14]1.[OH-].[Na+]>C1(C)C=CC=CC=1>[NH2:12][C:13]1([CH3:27])[C:17]2([CH2:19][CH2:18]2)[CH2:16][N:15]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:14]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131728788(-)-7-Amino-5-benzyl-7-methyl-5-azaspiro[2.4]heptane d-mandelate

Product 1

HCID 249623127-Amino-5-benzyl-7-methyl-5-azaspiro[2.4]heptaneYield 122.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To (−)-7-amino-5-benzyl-7-methyl-5-azaspiro[2.4]heptane D-mandelate (22.43 g, optical purity: 98% e.e.), 10% Aqueous sodium hydroxide and toluene were added, and the mixture was stirred at room temperature. Thereafter, the toluene layer was separated, washed with saturated brine, and dried with sodium sulfate. The desiccant was removed through filtration, and the filtrate was concentrated under reduced pressure, to thereby yield the title product as pale yellow oil (16.13 g, optical purity: 98% e.e.).

Workup

  1. customThereafter, the toluene layer was separated
  2. washwashed with saturated brine
  3. dry with materialdried with sodium sulfate
  4. customThe desiccant was removed through filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-67bbdb64c2d343cda133dd9b687fdb12
Source dataset
uspto-grants-2013_02
Patent number
US08378119B2

Reaction notes

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