Hydrochloric Acid → HCID 131725774, compound

HRID 1827303Notes

Reaction equation

HRID 1827303 reaction equation
[BH4-].[Na+].C([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C@@H:13]1[O:27][C@:17]2([CH2:28][O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C@@:18]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([OH:19])[C@H:14]1[O:15][CH2:16]2)C=C.Cl>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCCC1>[CH2:20]([C@@:18]1([OH:19])[C@@:17]2([CH2:16][O:15][C@H:14]1[C@H:13]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[OH:6])[O:27]2)[CH2:28][O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 131725775HCID 131725775, compound

Product 1

HCID 131725774HCID 131725774, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Tetrakis(triphenylphosphine)palladium(0) (173 mg, 0.15 mmol) and sodium tetrahydroborate (260 mg, 6.9 mmols) were added to an anhydrous tetrahydrofuran (20 ml) solution of the compound (23) (1.05 g, 2.3 mmols), and the mixture was stirred for 8 hours at room temperature. After 1N hydrochloric acid was added, the system was extracted with ethyl acetate 3 times. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to obtain colorless crystals (24) (755 mg, 79%).

Workup

  1. extractionthe system was extracted with ethyl acetate 3 times
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-49e4ab7f3e1a416a96d603842755eb79
Source dataset
uspto-grants-2006_05
Patent number
US07053199B2

Reaction notes

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