Water → 5-((R)-alpha-methylbenzyl)-7-hydroxy-5-azaspiro[2.4]heptane

HRID 1969408Notes

Reaction equation

HRID 1969408 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C@@H:8]([N:15]1[CH2:21][C:20](=[O:22])[C:17]2([CH2:19][CH2:18]2)[C:16]1=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(OCC)(=O)C.O>C1COCC1>[CH3:7][C@@H:8]([N:15]1[CH2:21][CH:20]([OH:22])[C:17]2([CH2:18][CH2:19]2)[CH2:16]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11775986HCID 11775986, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 228504715-((R)-alpha-methylbenzyl)-7-hydroxy-5-azaspiro[2.4]heptaneYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of LiAlH4 (0.995 g, 26.2 mmol) in THF (40 mL) was added a solution of 5-((R)-α-methylbenzyl)-4,7-dioxo-5-azaspiro[2.4]heptane (3.0 g, 13.1 mmol) in THF (10 mL) at 0° C. The reaction mixture was stirred at 0° C. for 2 hrs, then warmed up to 50° C. and continued to stir for 6 hrs. The reaction mixture was then cooled to 0° C. and ethyl acetate (10 mL) and water (10 mL) were added. The suspension was filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (1:3 (v/v) 2-butanol/n-hexane) to afford the title compound as colorless oil (2.4 g, 85%).

Workup

  1. temperaturewarmed up to 50° C.
  2. stirringto stir for 6 hrs
  3. temperatureThe reaction mixture was then cooled to 0° C.
  4. filtrationThe suspension was filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (1:3 (v/v) 2-butanol/n-hexane)

Sources & evidence

ORD record
ord-ce98375d32954819979d9c801804d72f
Source dataset
uspto-grants-2013_04
Patent number
US08426585B2

Reaction notes

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