Acetic Acid → HCID 57545194, compound

HRID 1661522Notes

Reaction equation

HRID 1661522 reaction equation
C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C.[Br:23][C:24]1[CH:29]=[CH:28][C:27]([C@:30]23[C@H:37]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH2:36][C:35](=[O:44])[C@@:34]2([OH:45])[C:33]2[C:46]([O:53][CH2:54][CH3:55])=[CH:47][C:48]([O:50][CH2:51][CH3:52])=[CH:49][C:32]=2[O:31]3)=[CH:26][CH:25]=1.C(=O)(O)[O-].[Na+]>C(#N)C>[Br:23][C:24]1[CH:29]=[CH:28][C:27]([C@:30]23[C@H:37]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH2:36][C@@H:35]([OH:44])[C@@:34]2([OH:45])[C:33]2[C:46]([O:53][CH2:54][CH3:55])=[CH:47][C:48]([O:50][CH2:51][CH3:52])=[CH:49][C:32]=2[O:31]3)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 57545180HCID 57545180, compound

Product 1

HCID 57545194HCID 57545194, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

1.2 ml of glacial acetic acid are added to 814 mg (3.09 mmol) of tetramethylammonium triacetoxyborohydride in 1.2 ml of acetonitrile under argon, and the mixture is stirred at RT for 0.5 h. Then 105 mg (0.21 mmol) of (3S*,3aR*,8bR*)-3a-(4-bromophenyl)-6,8-diethoxy-8b-hydroxy-3-phenyl-2,3,3a,8b-tetrahydrocyclopenta[b]benzofuran-1-one are added dropwise as solution in 12 ml of acetonitrile. The mixture is stirred at RT overnight. At 0° C., saturated sodium bicarbonate solution is added to the reaction mixture, the aqueous phase is extracted twice with dichloromethane, and the combined organic phases are dried over sodium sulfate, filtered and concentrated. Gradient chromatography on silica gel 60 (mobile phase: toluene/ethyl acetate) results in 77 mg (71% of theory) of the product as racemic mixture.

Workup

  1. stirringThe mixture is stirred at RT overnight
  2. extractionthe aqueous phase is extracted twice with dichloromethane
  3. dry with materialthe combined organic phases are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customGradient chromatography on silica gel 60 (mobile phase: toluene/ethyl acetate) results in 77 mg (71% of theory) of the product as racemic mixture

Sources & evidence

ORD record
ord-8cf9e732033d49e688760ac7b5565039
Source dataset
uspto-grants-2011_10
Patent number
US08030347B2

Reaction notes

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