Hydrazine hydrate (1:1) → HCID 77230617, compound

HRID 1476930Notes

Reaction equation

HRID 1476930 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH:13]([O:26][CH2:27][CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:14][N:15]1C(=O)C2C(=CC=CC=2)C1=O.O.NN>C(O)C>[NH2:3][CH2:12][CH:13]([O:26][CH2:27][CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:33])[CH3:35])[CH2:14][NH2:15]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67976238Tert-butyl 2-(1,3-bis(1,3-dioxoisoindolin-2-yl)propan-2-yloxy)ethylcarbamate

Product 1

HCID 77230617HCID 77230617, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
42.5 °C

Procedure

A 20 L 4-neck round-bottom flask was flushed with N2. Then charged a solution of tert-butyl 2-(1,3-bis(1,3-dioxoisoindolin-2-yl)propan-2-yloxy)ethylcarbamate (919 g, 1.9 mol, 1.0 eq) in ethanol (12000 mL, 13.0 v), followed by dropwise addition of hydrazine hydrate (602 g, 12.0 mol, 6.3 eq) with stirring at 40-45° C. over 30 min. The resulting mixture was stirred for 7 hours at 40-45° C. in an oil bath. The reaction progress was monitored with LCMS. The reaction mixture was cooled to 20˜30° C. and filtered. The filtrate was concentrated under vacuum to give 424.0 g (97.5%) of tert-butyl 2-(1,3-diaminopropan-2-yloxy)ethylcarbamate as a brown oil.

Workup

  1. customA 20 L 4-neck round-bottom flask was flushed with N2
  2. stirringThe resulting mixture was stirred for 7 hours at 40-45° C. in an oil bath
  3. temperatureThe reaction mixture was cooled to 20˜30° C.
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-0ea79bb029824656ae1dccbfd2123ea4
Source dataset
uspto-grants-2016_08
Patent number
US09402914B2

Reaction notes

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