Hydrochloric Acid → 7-Amino-5-benzyl-4-oxo-7-methyl-5-azaspiro[2.4]heptane

HRID 1096559Notes

Reaction equation

HRID 1096559 reaction equation
[CH2:1]([N:8]1[CH2:14][C:13]([NH:16]C(OC(C)(C)C)=O)([CH3:15])[C:10]2([CH2:12][CH2:11]2)[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O>C1(C)C=CC=CC=1>[NH2:16][C:13]1([CH3:15])[C:10]2([CH2:12][CH2:11]2)[C:9](=[O:24])[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 577586535-Benzyl-7-t-butoxycarbonylamino-4-oxo-7-methyl-5-azaspiro[2.4]heptane

Product 1

HCID 575873067-Amino-5-benzyl-4-oxo-7-methyl-5-azaspiro[2.4]heptaneYield 90.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Benzyl-7-t-butoxycarbonylamino-4-oxo-7-methyl-5-azaspiro[2.4]heptane (43.63 g) was dissolved in toluene, and the solution was stirred under ice-cooling. 37% Concentrated hydrochloric acid (100 mL) was added dropwise thereto, followed by stirring. After 0.5 hours, water was added to the reaction mixture. The mixture was stirred and left to stand so as to separate the aqueous layer from the organic layer. Sodium hydroxide (54 g) was added to and dissolved in the separated aqueous layer so as to alkalify the layer. The aqueous layer was extracted several times with toluene repeatedly. All the toluene layers were combined and washed with saturated brine. The washed toluene layer was dried with sodium sulfate, followed by filtration. The filtrate was concentrated under reduced pressure, to thereby yield the title product (21.29 g, yield: 90.2%).

Workup

  1. temperaturecooling
  2. stirringby stirring
  3. stirringThe mixture was stirred
  4. waitleft
  5. customto separate the aqueous layer from the organic layer
  6. additionSodium hydroxide (54 g) was added to and
  7. dissolutiondissolved in the separated aqueous layer so as
  8. extractionThe aqueous layer was extracted several times with toluene repeatedly
  9. washwashed with saturated brine
  10. dry with materialThe washed toluene layer was dried with sodium sulfate
  11. filtrationfollowed by filtration
  12. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8f1a91673a2a4ed6be6d7fdba3f6a24f
Source dataset
uspto-grants-2012_03
Patent number
US08138352B2

Reaction notes

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