Hydrazine hydrate (1:1) → (S,S)-2-hydroxycyclopentanecarboxylic Hydrazide

Participants

Reaction Steps

To a 50-mL four-necked flask were added 2.33 g (16.2 mmol) of methyl (S,S)-2-hydroxycyclopentanecarboxylate and 9.3 ml of 2-propanol and stirring was started. Hydrazine monohydrate (1.62 g; (32.3 mmol) was dropped thereinto at 23° C. taking 30 minutes. After the dropping, the mixture was stirred at 85° C. for 15 hours. Followed by, heating was stopped and the mixture was cooled down to room temperature to precipitate the crystals. The crystals were filtered and washed with a small amount of 2-propanol. The resulting crystals were dried to give 1.50 g of the title compound. The yield was 63%. Ratio of anti-form to syn-form of the compound was measured by the same manner as in Example 4 and found that the anti/syn ratio was more than 99/1.

Provenance & Evidence