Ethyl Acetate → HCID 10424642, compound

HRID 233531Notes

Reaction equation

HRID 233531 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[C:10]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[N:9]=[CH:8]1)=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOC(C)=O>C1COCC1>[NH2:1][CH2:4][CH2:5][CH2:6][N:7]1[C:11]([C:12]2[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=2)=[C:10]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[N:9]=[CH:8]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10358746HCID 10358746, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10424642HCID 10424642, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The compound of example 3, described above (254 mg, 0.79 mmol), was dissolved in THF (2 mL) an added dropwise to a 0° solution of 1 N LiAlH4 in THF (1.2 mL, 1.2 mmol), stirred at 0° for 15 min, EtOAc (4 mL) was carefully added and the mixture was added to ice cold 10% NaOH (15 mL) and the product was extracted with EtOAc (4×25 mL), dried (K2CO3) and concentrated to a waxy solid, (175 mg, 75%). mp=81°-82°.

Workup

  1. extractionthe product was extracted with EtOAc (4×25 mL)
  2. dry with materialdried (K2CO3)
  3. concentrationconcentrated to a waxy solid, (175 mg, 75%)

Sources & evidence

ORD record
ord-94782b2a5113482fb4ad4e718cc932d8
Source dataset
uspto-grants-1997_01
Patent number
US05593991

Reaction notes

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