Water → HCID 68527763, compound

HRID 657539Notes

Reaction equation

HRID 657539 reaction equation
C(OC(=O)[NH:5][CH2:6][CH:7]1[C:10]2=[CH:11][C:12]3[O:16][CH2:15][O:14][C:13]=3[CH:17]=[C:9]2[CH2:8]1)C.O.[OH-].[Na+]>O1CCCC1>[O:14]1[C:13]2[CH:17]=[C:9]3[CH2:8][CH:7]([CH2:6][NH2:5])[C:10]3=[CH:11][C:12]=2[O:16][CH2:15]1

Participants

5

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 131729319HCID 131729319, compound

Product 1

HCID 68527763HCID 68527763, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

7.5 g (30 mmoles) of the product of Step 1 are dissolved in 15 mL of anhydrous tetrahydrofuran. The solution is poured dropwise into a suspension comprising 1.48 g (1.3 equivalents) of AlLiH4 suspended in 38 mL of anhydrous tetrahydrofuran. Stirring is carried out at 25° C. for 2 hours. The mixture is hydrolysed in the cold state using 2.7 mL of water, 2.7 mL of NaOH (20%) and then 2.7 mL of water. Filtration and evaporation of the filtrate to dryness are carried out. There are obtained 2.4 g of a residue which is purified by column chromatography over silica (eluant: CH2Cl2/ethanol/NH4OH: 95/5/0.5. The expected product is obtained in the form of a brown oil.

Workup

  1. filtrationFiltration and evaporation of the filtrate to dryness

Sources & evidence

ORD record
ord-815fb177dc53488fa3348f9ca4d0620c
Source dataset
uspto-grants-2011_12
Patent number
US08076325B2

Reaction notes

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