Tetrabutylammonium Fluoride → HCID 22242832, compound

HRID 891596Notes

Reaction equation

HRID 891596 reaction equation
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[O:24][CH:25]=[C:26]([C:28]#[N:29])[N:27]=2)[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:28]([C:26]1[N:27]=[C:23]([N:21]2[CH2:22][CH:19]([OH:18])[CH2:20]2)[O:24][CH:25]=1)#[N:29]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22243005HCID 22243005, compound

Product 1

HCID 22242832HCID 22242832, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-cyano-1,3-oxazol-2-yl)azetidine (0.61 g, 1.51 mmol) (obtained as described in Reference Example 23(1)) in tetrahydrofuran (30 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (1.5 ml) in an ice bath, and the mixture was stirred for 1 hour. After checking the completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate as the eluant to afford 1-(4-cyano-1,3-oxazol-2-yl)-3-hydroxyazetidine (0.21 g, yield 86%) as a white solid.

Workup

  1. customthe completion of the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-b24c643fe25047c9baf16f945d51fe53
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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