Acetic Acid → HCID 68546803, compound

HRID 30772Notes

Reaction equation

HRID 30772 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][C@@H:16]([CH3:26])[C@@H:17]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[OH:18].[CH:27]([C:30]1[CH:31]=[C:32]([C:40]2[CH:45]=[C:44]([CH3:46])[C:43]([O:47][CH2:48][C:49](=O)[CH3:50])=[C:42]([CH3:52])[CH:41]=2)[CH:33]=[CH:34][C:35]=1[C:36]([O:38][CH3:39])=[O:37])([CH3:29])[CH3:28].C(O)(=O)C>O1CCCC1>[OH:18][C@H:17]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[C@@H:16]([NH:15][CH:49]([CH3:50])[CH2:48][O:47][C:43]1[C:42]([CH3:52])=[CH:41][C:40]([C:32]2[CH:33]=[CH:34][C:35]([C:36]([O:38][CH3:39])=[O:37])=[C:30]([CH:27]([CH3:28])[CH3:29])[CH:31]=2)=[CH:45][C:44]=1[CH3:46])[CH3:26]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 6931143P-HydroxynorephedrineHCID 23090746Methyl 3-isopropyl-3',5'-dimethyl-4'-(2-oxopropoxy)biphenyl-4-carboxylate

Product 1

HCID 68546803HCID 68546803, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium triacetoxyborohydride (0.23 g) was added to a mixture of 4-((1R,2S)-2-amino-1-hydroxypropyl)phenol (0.082 g), methyl 3-isopropyl-3′,5′-dimethyl-4′-(2-oxo-propoxy)biphenyl-4-carboxylate (0.17 g) and acetic acid (0.03 mL) in tetrahydrofuran (2.5 mL) at room temperature with stirring, and the mixture was stirred at 50° C. for 4 hrs. After being cooled to room temperature, the reaction mixture was partitioned between a saturated aqueous solution of sodium bicarbonate and ethyl acetate. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:methylene chloride/methanol=9/1) followed by aminopropyl silica gel column chromatography (eluent:hexane/ethyl acetate=4/1) to afford methyl 4′-{(2RS)-2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)1-methylethylamino]propoxy}-3-isopropyl-3′,5′-dimethylbiphenyl-4-carboxylate (0.074 g).

Workup

  1. stirringthe mixture was stirred at 50° C. for 4 hrs
  2. customthe reaction mixture was partitioned between a saturated aqueous solution of sodium bicarbonate and ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent:methylene chloride/methanol=9/1)

Sources & evidence

ORD record
ord-c885be749bce431ab913fa3e471d367a
Source dataset
uspto-grants-2008_09
Patent number
US07423185B2

Reaction notes

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