Sodium borohydride → HCID 57577369, compound

HRID 1921691Notes

Reaction equation

HRID 1921691 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6](=[O:36])[C:7]([NH:32][C:33](=[O:35])[CH3:34])([CH:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:19]=2)[C:14]1=[O:31])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4]>C(O)C>[CH2:3]([O:5][C:6](=[O:36])[C:7]([NH:32][C:33](=[O:35])[CH3:34])([CH:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:19]=2)[CH:14]1[OH:31])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57577370Diethyl acetamido(6-octyl-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)propanedioate2×

Product 1

HCID 57577369HCID 57577369, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of sodium borohydride (75 mg, 2.00 mmol) in 5 ml of ethanol at room temperature is added 2-acetylamino-2-(6-octyl-1-oxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-malonic acid diethyl ester (compound 5) (1.00 g, 2.1 mmol) in 5 ml of ethanol. The reaction mixture is stirred at room temperature under argon for an additional hour, quenched by the addition of water (20 mL) and methylene chloride (20 mL). The organic layer is removed and the aqueous layer is extracted with methylene chloride (2×20 mL). The combined organic layers were washed with brine (2×20 mL) and dried over magnesium sulfate and concentrated under vacuum. The residue is purified by column chromatography (silica gel, 20% ethyl acetate in hexanes) to provide 755 mg of compound A (75%).

Workup

  1. customquenched by the addition of water (20 mL) and methylene chloride (20 mL)
  2. customThe organic layer is removed
  3. extractionthe aqueous layer is extracted with methylene chloride (2×20 mL)
  4. washThe combined organic layers were washed with brine (2×20 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue is purified by column chromatography (silica gel, 20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-32b0801000f94920870d7ca21932cfb3
Source dataset
uspto-grants-2012_05
Patent number
US08173710B2

Reaction notes

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