Reaction #81080

Reaction equation

(S)-2-Phthalimido-5,5-dimethoxypentanoic acid, methyl ester

hydrazine monohydrate

→

title product

(S)-2-Amino-5,5-dimethoxypentanoic acid, methyl ester

Solvents

methanol

Conditions

Workup

1. 1
   FiltrationThe mixture was filtered
2. 2
   Washthe solid was washed with methanol
3. 3
   ConcentrationThe filtrate was concentrated
4. 4
   Othertriturated with methylene chloride
5. 5
   Filtrationfiltered again
6. 6
   Concentrationconcentrated
7. 7
   Otherdried in vacuo
8. 8
   Otherto yield 1.89 g

Procedure

(S)-2-Phthalimido-5,5-dimethoxypentanoic acid, methyl ester [prepared as described in Example 4(f), 3.35 g., 10.43 mmol.) in methanol (70 ml.) was treated with hydrazine monohydrate (531 μl., 10.95 mmol., 1.05 eq.) and the solution was stirred at room temperature for 6 days. The mixture was filtered and the solid was washed with methanol. The filtrate was concentrated, triturated with methylene chloride, filtered again, concentrated, and dried in vacuo to yield 1.89 g. of title product as a cloudy oil. TLC (10% methanol in methylene chloride) Rf =0.39.

Source