Hydrochloric Acid → HCID 17862026, compound

HRID 1785360Notes

Reaction equation

HRID 1785360 reaction equation
[CH3:1][N:2]([CH3:22])[C:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([OH:19])[CH2:13][C:14](OCC)=[O:15])=[C:8]([CH:20]=[CH2:21])[CH:7]=1)=[O:4].[BH4-].[Li+].O.Cl>O1CCCC1>[CH3:22][N:2]([CH3:1])[C:3](=[O:4])[O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([OH:19])[CH2:13][CH2:14][OH:15])=[C:8]([CH:20]=[CH2:21])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4148881Lithium borohydrideHCID 17861959HCID 17861959, compound

Product 1

HCID 17862026HCID 17862026, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(4-dimethylcarbamoyloxy-2-vinyl-phenyl)-3-hydroxy-propionate (5.28 g, 17.2 mmol) obtained in step (d) of Example 192 in tetrahydrofuran (50 ml) was added lithium tetrahydroborate (544 mg, 25.0 mmol) at −20° C. with stirring, and the reaction temperature was raised gradually to ambient temperature over one hour under a nitrogen atmosphere. To the reaction mixture were added successively water (20 ml) and 1N hydrochloric acid (20 ml), and the resulting mixture was extracted with ethyl acetate (40 ml×2). The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo to afford the crude product. The crude product was purified by chromatography on a silica gel column using mixed solvents of hexane and ethyl acetate (1:1-0:1) and ethyl acetate and methanol (5:1) successively as the eluents to afford the title compound (4.44 g, yield: 97%) as a colorless oil.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (40 ml×2)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customto afford the crude product
  6. customThe crude product was purified by chromatography on a silica gel column
  7. additionusing mixed solvents of hexane and ethyl acetate (1:1-0:1) and ethyl acetate and methanol (5:1) successively as the eluents

Sources & evidence

ORD record
ord-e4ed07f7214b4021a98263981ed2fc2c
Source dataset
uspto-grants-2009_03
Patent number
US07504437B2

Reaction notes

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