Sodium Hydroxide → (7S)-7-Amino-5-benzyl-5-azaspiro[2.4]heptan-4-one

HRID 1071844Notes

Reaction equation

HRID 1071844 reaction equation
C([C@@H]([C@H](C(O)=O)O)O)(O)=O.[NH2:11][C@H:12]1[C:16]2([CH2:18][CH2:17]2)[C:15](=[O:19])[N:14]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13]1.[OH-].[Na+]>C1(C)C=CC=CC=1>[NH2:11][C@H:12]1[C:16]2([CH2:18][CH2:17]2)[C:15](=[O:19])[N:14]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69590804HCID 69590804, compound

Product 1

HCID 11424478(7S)-7-Amino-5-benzyl-5-azaspiro[2.4]heptan-4-oneYield 74.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 14.3 g of (S)-7-amino-4-oxo-5-benzyl-5-azaspiro[2.4]heptane L-tartrate prepared in Example 4 was added and stirred 85.8 g of toluene, followed by dropwise addition of 23.4 g of 20% by weight sodium hydroxide aqueous solution at a temperature of 30° C. or lower. After separation, the toluene layer was adjusted to have pH11.6 to 12.0 with a concentrated hydrochloric acid, was concentrated under reduced pressure and thereby yielded 6.3 g of (S)-7-amino-4-oxo-5-benzyl-5-azaspiro[2.4]heptane.

Workup

  1. customAfter separation
  2. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-8ea6774aae414bd2b27da9727092d547
Source dataset
uspto-grants-2005_06
Patent number
US06906197B2

Reaction notes

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