Acetic Acid → 1-(8-Methyl-1,4-dioxa-spiro[4.5]dec-8-yl)-pyrrolidin-2-one

HRID 2235220Notes

Reaction equation

HRID 2235220 reaction equation
[O:1]=[C:2](N1CCOC1=O)[CH2:3][CH2:4][CH:5]=O.[CH3:13][C:14]1([NH2:24])[CH2:23][CH2:22][C:17]2([O:21][CH2:20][CH2:19][O:18]2)[CH2:16][CH2:15]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O>[CH3:13][C:14]1([N:24]2[CH2:5][CH2:4][CH2:3][C:2]2=[O:1])[CH2:23][CH2:22][C:17]2([O:18][CH2:19][CH2:20][O:21]2)[CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 106072654-Oxo-4-(2-oxo-oxazolidin-3-yl)-butyraldehydeHCID 211341968-Methyl-1,4-dioxaspiro[4.5]decan-8-amine

Product 1

HCID 684700351-(8-Methyl-1,4-dioxa-spiro[4.5]dec-8-yl)-pyrrolidin-2-oneYield 9%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

Dissolve 4-oxo-4-(2-oxo-oxazolidin-3-yl)-butyraldehyde (7.35 g, 42.96 mmol) in DCE (400 mL). Add 8-methyl-1,4-dioxa-spiro[4.5]dec-8-ylamine (7.36 g, 42.96 mmol), and acetic acid (2.58 g, 42.96 mmol) at room temperature under nitrogen. Stir the solution for one hour and then add sodium triacetoxyborohydride (18.21 g, 85.92 mmol). Stir the reaction mixture for over night and then add water (400 mL). Extract the aqueous layer with dichloromethane (3×400 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 20-50% of EtOAc-Hexane) to give 0.92 g (9.0%) of 1-(8-Methyl-1,4-dioxa-spiro[4.5]dec-8-yl)-pyrrolidin-2-one as a colorless oil.

Workup

  1. customat room temperature
  2. stirringStir the reaction mixture for over night
  3. extractionExtract the aqueous layer with dichloromethane (3×400 mL)
  4. dry with materialCombine the organic layers and dry with Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. custompurify by flash column chromatography (silica gel, 20-50% of EtOAc-Hexane)

Sources & evidence

ORD record
ord-5e21d6d609904d63879f8b9f433e961a
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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