Sodium Bicarbonate → HCID 86617195, compound

HRID 1993489Notes

Reaction equation

HRID 1993489 reaction equation
[OH:1][C@H:2]1[C@H:15]([NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14]2[CH:13]=[C:12]3[C:7]([O:8][CH2:9][C:10](=O)[NH:11]3)=[CH:6][C:5]=2[O:4][C:3]1([CH3:27])[CH3:26].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)([O-])O.[Na+]>>[CH3:26][C:3]1([CH3:27])[C@@H:2]([OH:1])[C@H:15]([NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14]2[CH:13]=[C:12]3[C:7]([O:8][CH2:9][CH2:10][NH:11]3)=[CH:6][C:5]=2[O:4]1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 86617193HCID 86617193, compound

Product 1

HCID 86617195HCID 86617195, compoundYield 59%

Conditions

Temperature
90 °C

Procedure

To (±)-trans-7-hydroxy-6,6-dimethyl-8-(2-phenylethylamino)-7,8-dihydro-1H,6H-4,5-dioxa-1-aza-anthracene-2-one (67 mg, 0.18 mmol), lithium aluminum hydride (1M solution in tetrahydrofuran, 910 μL, 0.91 mmol) was added at room temperature, and the resulting mixture was stirred at 90° C. for 0.5 hour. Upon the completion of the reaction, saturated sodium hydrogencarbonate aqeuous solution was added thereto, the resulting solution was extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The resulting mixture was purified by silica gel column (ethyl acetate) and the aimed product was obtained (yield: 59%).

Workup

  1. additionwas added
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting mixture was purified by silica gel column (ethyl acetate)

Sources & evidence

ORD record
ord-2d3385ba89b5457ebd5aee1ca24161e9
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

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