Methylhydrazine → 1-Boc-1-(2-isopropoxyethyl)hydrazine
Reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[N:12]([CH2:20][CH2:21][O:22][CH:23]([CH3:25])[CH3:24])[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].CNN>O1CCCC1>[CH:23]([O:22][CH2:21][CH2:20][N:12]([C:13]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:19])[NH2:3])([CH3:25])[CH3:24]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of tert-butyl 1,3-dioxoisoindolin-2-yl(2-isopropoxyethyl)carbamate (example 77B, 1.262 g, 3.62 mmol) in tetrahydrofuran (24.15 mL) at 0° C. was slowly added methylhydrazine (0.289 mL, 5.43 mmol). The reaction mixture was stirred at 0° C. for 3 h. The reaction mixture was filtered to remove the white precipitate and the filtrate was concentrated in vacuo. The semisolid was triturated with ethyl acetate (2×) and the triturant was concentrated in vacuo. This process was repeated to ultimately provide tert-butyl 1-(2-isopropoxyethyl)hydrazinecarboxylate (0.665 g, 84% yield) as a yellow oil.
Workup
- customat 0° C.
- filtrationThe reaction mixture was filtered
- customto remove the white precipitate
- concentrationthe filtrate was concentrated in vacuo
- customThe semisolid was triturated with ethyl acetate (2×)
- concentrationthe triturant was concentrated in vacuo
Sources & evidence
- ORD record
- ord-ee7a7309113643a4911319d078222b19
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202881B2
Reaction notes
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