Hydrazine hydrate (1:1) → (2R)-oxolane-2-carbohydrazide

HRID 541288Notes

Reaction equation

HRID 541288 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.Cl.C1C=CC2N(O)[N:28]=[N:27]C=2C=1.O.NN>ClCCl>[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[C:6]([NH:27][NH2:28])=[O:8]

Participants

6

Reactant 4

HCID 24654Hydrazine hydrate (1:1)HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734707Tetrahydro-2-furoic acid, (+)-

Product 1

HCID 40566306(2R)-oxolane-2-carbohydrazideYield 59.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a round-bottom flask was added a solution of (R)-tetrahydrofuran-2-carboxylic acid (3.00 g, 25.8 mmol, 1.00 equiv) in dichloromethane (60 mL). EDC.HCl (7.37 g, 38.5 mmol, 1.50 equiv), HOBt (5.24 g, 38.8 mmol, 1.50 equiv), and hydrazine hydrate (2.60 g, 51.9 mmol, 2.00 equiv) were added to the reaction. The resulting solution was stirred overnight at 25° C. The solids were removed with filtration. The filtrate was concentrated in vacuo to yield 2.00 g (59%) of (R)-tetrahydrofuran-2-carbohydrazide as a yellow oil.

Workup

  1. customThe solids were removed with filtration
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3bff4fe272fe451c990ef9e6a97ec23a
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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