Methanol → 9-[4-(5-Cyano-pyridin-2-yloxymethyl)-3,3-dimethyl-2-oxo-pyrrolidin-1-yl]-bicyclo[3.3.1]nonane-3-carboxylic acid

HRID 2115621Notes

Reaction equation

HRID 2115621 reaction equation
[Li+].[OH-].C[O:4][C:5]([CH:7]1[CH2:14][CH:13]2[CH:15]([N:16]3[CH2:20][CH:19]([CH2:21][O:22][C:23]4[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][N:24]=4)[C:18]([CH3:32])([CH3:31])[C:17]3=[O:33])[CH:9]([CH2:10][CH2:11][CH2:12]2)[CH2:8]1)=[O:6].CO.O>O1CCCC1>[C:29]([C:26]1[CH:27]=[CH:28][C:23]([O:22][CH2:21][CH:19]2[CH2:20][N:16]([CH:15]3[CH:9]4[CH2:10][CH2:11][CH2:12][CH:13]3[CH2:14][CH:7]([C:5]([OH:6])=[O:4])[CH2:8]4)[C:17](=[O:33])[C:18]2([CH3:32])[CH3:31])=[N:24][CH:25]=1)#[N:30]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 666569249-[4-(5-Cyano-pyridin-2-yloxymethyl)-3,3-dimethyl-2-oxo-pyrrolidin-1-yl]-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

Product 1

HCID 666569469-[4-(5-Cyano-pyridin-2-yloxymethyl)-3,3-dimethyl-2-oxo-pyrrolidin-1-yl]-bicyclo[3.3.1]nonane-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiOH (0.2 g, 4.84 mmol) was added in one portion to a stirred solution of the product of Example 7E (0.532 g, 1.21 mmol) in a mixture of tetrahydrofuran (6 mL), methanol (3 mL), and water (3 mL). The resulting solution was stirred overnight, followed by partitioning with diethyl ether and water. The organic layer was washed with water and the combined water layers were acidified with NaHSO4 solution and extracted with ethyl acetate. The combined ethyl acetate phases were dried (MgSO4), filtered, and evaporated. The acid product was used without further purification.

Workup

  1. customby partitioning with diethyl ether and water
  2. washThe organic layer was washed with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined ethyl acetate phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe acid product was used without further purification

Sources & evidence

ORD record
ord-81a9870c21a54b938f81c99c6bb01cad
Source dataset
uspto-grants-2008_10
Patent number
US07435833B2

Reaction notes

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