Hydrochloric Acid → HCID 10822001, compound

HRID 2215838Notes

Reaction equation

HRID 2215838 reaction equation
[NH2:1][C@H:2]1[C:6]2([CH2:8][CH2:7]2)[C:5](=O)[N:4]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3]1.[H-].COCCO[Al+]OCCOC.[Na+].[H-].Cl>C1(C)C=CC=CC=1>[NH2:1][C@H:2]1[C:6]2([CH2:8][CH2:7]2)[CH2:5][N:4]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11424478(7S)-7-Amino-5-benzyl-5-azaspiro[2.4]heptan-4-oneHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 10822001HCID 10822001, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent4×

Conditions

Temperature
45 °C

Procedure

Specifically, 6.3 g of (S)-7-amino-4-oxo-5-benzyl-5-azaspiro[2.4]heptane prepared in Example 5 was added to 31.5 g of toluene and was stirred at 45° C. To the mixture was added dropwise a mixture of 10.9 g of 65% by weight solution of sodium bis(2-methoxyethoxy)aluminum hydride in toluene and 12.6 g of toluene at a temperature of 75° C. or lower within 5 minutes. After the completion of addition, the mixture was stirred at 75° C. for 30 minutes and was cooled to 5° C. or below. To the cooled mixture was added 124.4 g of 10% by weight hydrochloric acid at a temperature of 20° C. or lower, the mixture was then diluted with 56.7 g of toluene and was separated. To the aqueous layer was added dropwise 122.3 g of 20% by weight sodium hydroxide aqueous solution at a temperature of 20° C. or lower. The mixture was diluted with 113.4 g of toluene and was separated, and the toluene layer was fractionated. The aqueous layer was extracted with 75.6 g of toluene, and the toluene layer was fractionated. These toluene layers were added together, were concentrated under reduced pressure and thereby yielded 3.7 g of (S)-7-amino-5-benzyl-5-azaspiro[2.4]heptane.

Workup

  1. additionTo the mixture was added dropwise
  2. additionAfter the completion of addition
  3. stirringthe mixture was stirred at 75° C. for 30 minutes
  4. temperaturewas cooled to 5° C. or below
  5. customwas separated
  6. additionTo the aqueous layer was added dropwise 122.3 g of 20% by weight sodium hydroxide aqueous solution at a temperature of 20° C.
  7. additionThe mixture was diluted with 113.4 g of toluene
  8. customwas separated
  9. extractionThe aqueous layer was extracted with 75.6 g of toluene
  10. additionThese toluene layers were added together
  11. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-543218723be446339500a0c346ce9676
Source dataset
uspto-grants-2006_09
Patent number
US07109350B2

Reaction notes

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