Water → HCID 59455752, compound

HRID 547803Notes

Reaction equation

HRID 547803 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][C@H:15]([O:17][Si](C(C)(C)C)(C)C)[CH2:14][C@H:13]([O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][C@H:15]([OH:17])[CH2:14][C@H:13]([O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 59455633HCID 59455633, compound

Product 1

HCID 59455752HCID 59455752, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2.3 g (5.0 mmol) (3S,5R)-3-benzoyloxy-5-(tert-butyl-dimethyl-silanyloxy)-piperidine-1-carboxylic acid benzyl ester in 20 ml dry THF were added 5.5 ml (5.5 mmol) of a 1M solution of tetrabutyl ammoniumfluoride in THF at 0° C. After completed addition, the mixture was allowed to warm to room temperature over 30 min. Addition of water was followed by extraction with three portions of tert-butyl methyl ether. The combined organic extracts were dried over sodium sulfate. Kugelrohr distillation gave 1.7 g (95%) of the title compound as a light yellow oil.

Workup

  1. additionaddition
  2. extractionwas followed by extraction with three portions of tert-butyl methyl ether
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. distillationKugelrohr distillation

Sources & evidence

ORD record
ord-144efbad88f2433394f99092477fb108
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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