Ammonium Chloride → 1-Hydroxy-spiro[4.5]decane-2-carboxylic acid methyl ester

HRID 2070555Notes

Reaction equation

HRID 2070555 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][C:7]2([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:6]1[O:15][Si](CC)(CC)CC)=[O:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][C:7]2([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[CH:6]1[OH:15])=[O:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 577713731-Triethylsiloxy-spiro[4.5]decane-2-carboxylic acid methyl ester

Product 1

HCID 577715401-Hydroxy-spiro[4.5]decane-2-carboxylic acid methyl esterYield 49.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-triethylsiloxy-spiro[4.5]decane-2-carboxylic acid methyl ester (5.0 g) obtained in Step 2 in tetrahydrofuran (30 mL) was added a 1M tetrahydrofuran solution of tetra-n-butylammonium fluoride (18.4 mL), followed by stirring the reaction mixture at room temperature for 30 minutes. Then, after addition of aqueous ammonium chloride solution, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=5:1) to give 1-hydroxy-spiro[4.5]decane-2-carboxylic acid methyl ester (less-polar isomer; 1.6 g, more-polar isomer; 0.95 g).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=5:1)

Sources & evidence

ORD record
ord-c68357da7ba34631beccb4df8b3d2a57
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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