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

HRID 1096565Notes

Reaction equation

HRID 1096565 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-9ab5c7c81e1b49aea3bdcc50794901a2
Source dataset
uspto-grants-2012_03
Patent number
US08138352B2

Reaction notes

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