HCID 15199513, compound → HCID 18950575, compound

HRID 1492416Notes

Reaction equation

HRID 1492416 reaction equation
ClC1C=CC(CN2C3C(=CC([O:16][CH2:17][C:18]4[N:23]=[C:22]5[C:24]([Cl:28])=[C:25]([Cl:27])[S:26][C:21]5=[CH:20][CH:19]=4)=CC=3)C(CC(C)(C)C)=C2CC(C)(C)C(O)=O)=CC=1.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[Cl:27][C:25]1[S:26][C:21]2[C:22](=[N:23][C:18]([CH2:17][OH:16])=[CH:19][CH:20]=2)[C:24]=1[Cl:28]

Participants

4

Reactant 2

HCID 15199513HCID 15199513, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 18950575HCID 18950575, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a -30° C. solution of the methyl ester (60 g, 230 mmol) of Step 1 in 2.2 L of THF was added diisobutylaluminum hydride (570 mmol) over 1 hr. The reaction mixture was brought to -25° C. and allowed to proceed for another 10 min. The reaction was quenched with an aqueous solution of sodium potassium tartrate (1750 mL of 30% w/v) and extracted with EtOAc. The organic phase was dried over Na2SO4, and the solvent evaporated. The crude product was swished in CH2Cl2 (100 mL) to give 42 g (78%) of the title alcohol as a light yellow solid.

Workup

  1. customwas brought to -25° C.
  2. customThe reaction was quenched with an aqueous solution of sodium potassium tartrate (1750 mL of 30% w/v)
  3. extractionextracted with EtOAc
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-b34d15b8b5de4d3b937deb0399606ee7
Source dataset
uspto-grants-1994_12
Patent number
US05374635

Reaction notes

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