Hydrazine → HCID 131729311, compound

HRID 657134Notes

Reaction equation

HRID 657134 reaction equation
[CH3:1][C:2]([Si:5]([CH3:36])([CH3:35])[O:6][C@H:7]1[CH2:12][C@@H:11]([CH2:13][N:14]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:10][N:9]([C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[CH2:8]1)([CH3:4])[CH3:3].NN>CCO>[NH2:14][CH2:13][C@H:11]1[CH2:12][C@@H:7]([O:6][Si:5]([C:2]([CH3:1])([CH3:4])[CH3:3])([CH3:36])[CH3:35])[CH2:8][N:9]([C:25]([O:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:26])[CH2:10]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 131729310HCID 131729310, compound

Product 1

HCID 131729311HCID 131729311, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To cis-phenylmethyl (3RS,5RS)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-1-piperidinecarboxylate (660 mg; 1.3 mmol) in EtOH (20 ml) was added anhydrous hydrazine (0.2 ml; 6.5 mmol). The reaction was allowed to stir at room temperature under nitrogen for 14 hours, and the reaction was filtered through a pad of Celite®. The filtrate was partitioned between EtOAc (150 ml) and water (50 ml), the layers were separated, and the organic layer was washed with brine and dried with Na2SO4. The solvents were removed to give the desired compound (450 mg; 92%) as a pale yellow oil which was used without further purification.

Workup

  1. filtrationthe reaction was filtered through a pad of Celite®
  2. customThe filtrate was partitioned between EtOAc (150 ml) and water (50 ml)
  3. customthe layers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried with Na2SO4
  6. customThe solvents were removed

Sources & evidence

ORD record
ord-11095ac3c285431ea717cc4cd7ad0843
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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