Ammonium Hydroxide → 2-Azaspiro(4.5)decan-1-one

HRID 2427467Notes

Reaction equation

HRID 2427467 reaction equation
C[O:2][C:3]([C:5]1([CH2:11][C:12]#[N:13])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=O.[BH4-].[Na+].[OH-].[NH4+]>C1COCC1.O.O.O.O.O.O.O.[Co](Cl)Cl>[C:3]1(=[O:2])[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:11][CH2:12][NH:13]1

Participants

7

Reactant 3

HCID 14923Ammonium HydroxideHCID 4311764Sodium borohydrideHCID 576578081-Cyanomethyl-cyclohexanecarboxylic acid methyl ester

Product 1

HCID 250672652-Azaspiro(4.5)decan-1-oneYield 54%

Reagents, catalysts & solvents 3

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 0° C. mixture of 1-cyanomethyl-cyclohexanecarboxylic acid methyl ester (4.28 g, 23.6 mmol) and cobalt (II) chloride hexahydrate (2.81 g, 11.8 mmol) in THF (80 mL) and water (40 mL) is treated portion-wise with sodium borohydride (4.47 g, 0.118 mol) and is warmed to room temperature and stirred for 48 hours under N2. The reaction is treated with 28% ammonium hydroxide (3.1 mL) and filtered through hyflo. The solvent is removed from the filtrate in vacuo and the residue is diluted with minimal water and brine and is extracted three times with 3:1 chloroform:isopropanol. The organic layer is dried (Na2SO4) and the solvent is removed in vacuo to afford crude product that is purified with a 0 to 10% methanol in CH2Cl2 gradient on silica gel to afford 1.95 g (54%) of the titled product. Rf=0.46 (9/1 CH2Cl2/methanol). MS (m/z): 154 (M+).

Workup

  1. filtrationfiltered through hyflo
  2. customThe solvent is removed from the filtrate in vacuo
  3. additionthe residue is diluted with minimal water and brine
  4. extractionis extracted three times with 3:1 chloroform
  5. dry with materialThe organic layer is dried (Na2SO4)
  6. customthe solvent is removed in vacuo
  7. customto afford crude product that
  8. customis purified with a 0 to 10% methanol in CH2Cl2 gradient on silica gel

Sources & evidence

ORD record
ord-bed85244ca7243c380e7309d2978f070
Source dataset
uspto-grants-2011_06
Patent number
US07968585B2

Reaction notes

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