Hydrazine → cis-3-(Tert-butyl-dimethyl-silanyloxy)-cyclopentylamine

HRID 1243172Notes

Reaction equation

HRID 1243172 reaction equation
[C:1]([Si:5]([CH3:24])([CH3:23])[O:6][C@@H:7]1[CH2:11][CH2:10][C@H:9]([N:12]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:8]1)([CH3:4])([CH3:3])[CH3:2].NN>C(O)C.O1CCCC1>[C:1]([Si:5]([CH3:24])([CH3:23])[O:6][C@@H:7]1[CH2:11][CH2:10][C@H:9]([NH2:12])[CH2:8]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86594646HCID 86594646, compound

Product 1

HCID 66877244cis-3-(Tert-butyl-dimethyl-silanyloxy)-cyclopentylamine

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a mixture of (±)-cis-2-[3-(tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-isoindole-1,3-dione (1.03 g, 2.98 mmol) (from Example 10b supra) in ethanol/tetrahydrofuran (2:1, 20 mL) was added anhydrous hydrazine (1.2 mL, 38.90 mmol) (Aldrich). After stirring overnight the reaction mixture was filtered. The solids were washed with diethyl ether (approx. 30 mL) and the combined filtrate was concentrated. The residue was treated with diethyl ether again (approx. 30 mL) and the resulting mixture was filtered again and concentrated to give (±)-cis-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentylamine as a colorless oil. (Yield 570 mg, 88%).

Workup

  1. filtrationwas filtered
  2. washThe solids were washed with diethyl ether (approx. 30 mL)
  3. concentrationthe combined filtrate was concentrated
  4. additionThe residue was treated with diethyl ether again (approx. 30 mL)
  5. filtrationthe resulting mixture was filtered again
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a5db8a0e8ca548798f1744a556280b21
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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