Hydrazine hydrate (1:1) → HCID 68108044, compound

HRID 1809677Notes

Reaction equation

HRID 1809677 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][CH:9]([N:15]1C(=O)C2C(=CC=CC=2)C1=O)[C:10]1[CH:14]=[CH:13][S:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].O.NN>C1COCC1.CO>[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][CH:9]([NH2:15])[C:10]1[CH:14]=[CH:13][S:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68108378[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-thiophen-3-yl-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 68108044HCID 68108044, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of [2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-thiophen-3-yl-ethyl]-carbamic acid tert-butyl ester (23 g, crude) in THF (100 mL) and methanol (100 mL) was added hydrazine hydrate (63 g, 1.26 mol). The mixture was heated at 60° C. for 2 hours and then cooled to 20° C. The reaction mixture was filtered and the filtration was concentrated to dryness. The residue was purified by column chromatography (methanol:dichloromethane, 1:50) to afford (2-amino-2-thiophen-3-yl-ethyl)-carbamic acid tert-butyl ester. (Yield 8.6 g, 57% for the two steps).

Workup

  1. temperaturecooled to 20° C
  2. filtrationThe reaction mixture was filtered
  3. filtrationthe filtration
  4. concentrationwas concentrated to dryness
  5. customThe residue was purified by column chromatography (methanol:dichloromethane, 1:50)

Sources & evidence

ORD record
ord-c9d6759e0ef54c1ba2c15d43cd190d7a
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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