Sodium Bicarbonate → HCID 69565154, compound

HRID 1815973Notes

Reaction equation

HRID 1815973 reaction equation
C([Si](C)(C)[O:6][C@H:7]([CH3:22])[CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]3[O:21][CH2:20][CH:19]=[CH:18][C:16]3=2)[CH:11]=[N:10]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)(O)[O-].[Na+]>C1COCC1>[N:9]1([CH2:8][C@H:7]([OH:6])[CH3:22])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]3[O:21][CH2:20][CH:19]=[CH:18][C:16]3=2)[CH:11]=[N:10]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 59683676HCID 59683676, compound

Product 1

HCID 69565154HCID 69565154, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the product from Example 4, Step B (0.26 g, 0.76 mmol) and tetrabutylammonium fluoride (1 M, 1.52 mmol) in THF (3 mL) was stirred at ambient temperature for 4 h. The reaction mixture was added to a saturated aqueous solution of sodium bicarbonate (10 mL) and this mixture was extracted with ethyl acetate (3×5 mL). The combined extracts were dried and evaporated to a residue which was purified by chromatography (silica, 10% to 40% ethyl acetate in hexane) to give the alcohol as an oil (0.14 g, 81%): LC/MS (+APCI) m/z 231 (M+H).

Workup

  1. extractionthis mixture was extracted with ethyl acetate (3×5 mL)
  2. customThe combined extracts were dried
  3. customevaporated to a residue which
  4. customwas purified by chromatography (silica, 10% to 40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-846330e4027a44fe90b575ff953fdf21
Source dataset
uspto-grants-2005_04
Patent number
US06881749B2

Reaction notes

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