Hydrazine hydrate (1:1) → HCID 86699613, compound

HRID 1053384Notes

Reaction equation

HRID 1053384 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][C@H:13]1[CH2:17][CH2:16][C@H:15]([CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:14]1.O.NN>>[NH2:3][O:12][C@H:13]1[CH2:17][CH2:16][C@H:15]([CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH2:14]1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86699612HCID 86699612, compound

Product 1

HCID 86699613HCID 86699613, compoundYield 73.7%

Procedure

A mixture of tert-butyl {trans-3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]cyclopentyl}methylcarbamate 115 (0.19 g, 0.53 mmol) was treated with hydrazine hydrate (0.03 g, 0.60 mmol). The mixture was stirred at room temperature for 2 hours. The solid was filtered off and the filtrate was concentrated in vacuo. The residue was diluted with DCM, and the insoluble solid was filtered off. The filtrate was concentrated in vacuo to give an oil which was purified by chromatography to give 116 (0.09 g, 44% over 2 steps) as a light yellow oil.

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionThe residue was diluted with DCM
  4. filtrationthe insoluble solid was filtered off
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto give an oil which
  7. customwas purified by chromatography

Sources & evidence

ORD record
ord-71c0d47da2c44400a413cf1cd364f59f
Source dataset
uspto-grants-2016_07
Patent number
US09393239B2

Reaction notes

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