Hydrochloric Acid → [9-(Prop-2-en-1-yl)-6-oxaspiro[4.5]decan-9-yl]hydrazine

HRID 76229Notes

Reaction equation

HRID 76229 reaction equation
C(O[NH:6][N:7]([C:12]1([CH2:22][CH:23]=[CH2:24])[CH2:21][C:16]2([CH2:20][CH2:19][CH2:18][CH2:17]2)[O:15][CH2:14][CH2:13]1)C(NN)=O)(C)(C)C.Cl>CCOC(C)=O.O1CCOCC1>[CH2:22]([C:12]1([NH:7][NH2:6])[CH2:21][C:16]2([CH2:20][CH2:19][CH2:18][CH2:17]2)[O:15][CH2:14][CH2:13]1)[CH:23]=[CH2:24]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68314800(tert-butoxy)-N'-[9-(prop-2-en-1-yl)-6-oxaspiro[4.5]decan-9-yl]carbohydrazide

Product 1

HCID 68314598[9-(Prop-2-en-1-yl)-6-oxaspiro[4.5]decan-9-yl]hydrazineYield 112.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (tert-butoxy)-N′-[9-(prop-2-en-1-yl)-6-oxaspiro[4.5]decan-9-yl]carbohydrazide (0.33 g, 1.06 mmol) in 4 mL of EtOAc was added 4M HCl in dioxane at rt. The solution was stirred at rt until reaction completion, monitored by LC-MS (30 h). The solvent was then removed to give [9-(prop-2-en-1-yl)-6-oxaspiro[4.5]decan-9-yl]hydrazine (250 mg). LCMS m/z 211.1 (M+1) observed.

Workup

  1. custommonitored by LC-MS (30 h)
  2. customThe solvent was then removed

Sources & evidence

ORD record
ord-c528d5f3f2a146bb85650f353aa99920
Source dataset
uspto-grants-2014_09
Patent number
US08835488B2

Reaction notes

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