Water → HCID 57771364, compound

HRID 2070598Notes

Reaction equation

HRID 2070598 reaction equation
[CH3:1][O:2][C:3](=[O:45])[CH2:4][C@@H:5]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH2:44][CH2:43][CH2:42][C@@:19]3([CH2:23][C@H:22]([O:24][Si](C(C)(C)C)(C4C=CC=CC=4)C4C=CC=CC=4)[CH2:21][CH2:20]3)[CH:18]=2)=[CH:11][CH:10]=1)[C:6]#[C:7][CH3:8].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[CH3:1][O:2][C:3](=[O:45])[CH2:4][C@@H:5]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH2:44][CH2:43][CH2:42][C@@:19]3([CH2:23][C@H:22]([OH:24])[CH2:21][CH2:20]3)[CH:18]=2)=[CH:11][CH:10]=1)[C:6]#[C:7][CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 57771542HCID 57771542, compound

Product 1

HCID 57771364HCID 57771364, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3S)-3-{4-[(2R,5R)-2-(tert-butyldiphenylsilanyloxy)-spiro[4.5]dec-6-en-7-ylmethoxy]-phenyl}-hex-4-ynoic acid methyl ester (738 mg) obtained in step 8 in tetrahydrofuran (3.7 mL) was added tetra-n-butylammonium fluoride (1M tetrahydrofuran solution; 2.97 mL), followed by stirring the mixture at room temperature for 17 hours. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:3) to give (3S)-3-[4-((2R,5R)-2-hydroxy-spiro[4.5]dec-6-en-7-ylmethoxy)-phenyl]-hex-4-ynoic acid methyl ester (395 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:3)

Sources & evidence

ORD record
ord-088f7f66df5e43399c3e40e82529bbcb
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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