Tetrabutylammonium Fluoride → HCID 11091194, compound

HRID 380641Notes

Reaction equation

HRID 380641 reaction equation
[O:1]([C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH2:21][CH2:22][C@@:23]([CH2:30][O:31][C:32](=[O:48])[N:33]([C:41]1[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=1)[C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)([OH:29])[CH2:24]2)[Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:40][C:37]1[CH:36]=[CH:35][C:34]([N:33]([C:41]2[CH:42]=[CH:43][C:44]([F:47])=[CH:45][CH:46]=2)[C:32]([O:31][CH2:30][C@@:23]2([OH:29])[CH2:22][CH2:21][C:20]3[C:25](=[CH:26][CH:27]=[CH:28][C:19]=3[OH:1])[CH2:24]2)=[O:48])=[CH:39][CH:38]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57311524HCID 57311524, compound

Product 1

HCID 11091194HCID 11091194, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of (2R)-5-t-butyldiphenylsiloxy-2-{[N,N-di(4-fluorophenyl)carbamoyloxy]methyl}-2-hydroxy-1,2,3,4-tetrahydronaphthalene in THF (1 ml) was added 1M-tetra-n-butylammonium fluoride solution in THF (0.77 ml) at room temperature. After stirring for 4 hours, the reaction mixture was partitioned between AcOEt and water. The organic layer was washed with 1N-HCl, water, and evaporated in vacuo. The residue was purified by chromatography on silica gel (25 ml) using a mixture of AcOEt and n-hexane (1:4) to give (2R)-2-{[N,N-di(4-fluorophenyl)carbamoyloxy]methyl}-2,5-dihydroxy-1,2,3,4-tetrahydronaphthalene (0.19 g) as an oil.

Workup

  1. customthe reaction mixture was partitioned between AcOEt and water
  2. washThe organic layer was washed with 1N-HCl, water
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel (25 ml)
  5. additiona mixture of AcOEt and n-hexane (1:4)

Sources & evidence

ORD record
ord-d005d8fbb3a54a91b149a8afb669b2a7
Source dataset
uspto-grants-2001_10
Patent number
US06303649B1

Reaction notes

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