Hydrazine → (2R)-oxolane-2-carbohydrazide
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
- stirringThe resulting mixture was stirred overnight at 25° C
- customThe solids were removed by filtration
- 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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