Hydrazine → (2R)-oxolane-2-carbohydrazide

HRID 541250Notes

Reaction equation

HRID 541250 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[C:6]([OH:8])=O.CCN=C=NCCCN(C)C.C1C=CC2N(O)[N:27]=[N:26]C=2C=1.NN>ClCCl>[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[C:6]([NH:26][NH2:27])=[O:8]

Participants

6

Conditions

Temperature
25 °C

Procedure

A mixture of (R)-tetrahydrofuran-2-carboxylic acid (5.00 g, 43.1 mmol, 1.00 equiv), EDCI (12.4 g, 64.6 mmol, 1.50 equiv) and HOBt (8.70 g, 64.4 mmol, 1.50 equiv) in dichloromethane (100 mL) was stirred for 30 min at 25° C. To the mixture was then added hydrazine (2.00 g, 62.4 mmol, 1.50 equiv) dropwise. The resulting mixture was stirred overnight at 25° C. The solids were removed by filtration, and the filtrate was concentrated in vacuo to furnish 25.0 g (crude) of (R)-tetrahydrofuran-2-carbohydrazide as a yellow oil.

Workup

  1. stirringThe resulting mixture was stirred overnight at 25° C
  2. customThe solids were removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-bbac68750f9f46808fa79290ea0f7700
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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