Hydrazine hydrate (1:1) → tert-butyl N-(2-amino-3-{[(tert-butoxy)carbonyl]amino}propyl)carbamate

HRID 459614Notes

Reaction equation

O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH:12]([CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].O.NN>C(O)C>[NH2:3][CH:12]([CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 5 °C

Procedure

Di-tert-butyl [2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1,3-propanediyl]biscarbamate (144 g) was suspended in ethanol (1.5 L), and hydrazine monohydrate (19.8 ml) was added dropwise to the suspension under cooling on an ice-water bath. The mixture was refluxed for 5 hours, and cooled to 5° C. on an ice-water bath. The precipitate was filtered off, and the filtrate was concentrated under reduced pressure and recrystallized from hexane (500 ml)—ethyl acetate (100 ml) to give di-tert-butyl (2-amino-1,3-propanediyl)biscarbamate (44.1 g) as crystals. The mother liquor (31.3 g), which proved to be satisfactorily pure by thin layer chromatography, was also used for the next reaction.

Workup

temperatureunder cooling on an ice-water bath
temperatureThe mixture was refluxed for 5 hours
filtrationThe precipitate was filtered off
concentrationthe filtrate was concentrated under reduced pressure
customrecrystallized from hexane (500 ml)—ethyl acetate (100 ml)

Sources & evidence

ORD record: ord-398949a87e624a7b96aafd94644fdb97
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192943B2

Reaction notes

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