Diethyl Ether → HCID 59382987, compound

HRID 1254335Notes

Reaction equation

HRID 1254335 reaction equation
[CH:1]1([C@H:6]([OH:29])[C@H:7]([N:18]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:8][N:9]([CH3:17])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.O.NN.CCOCC>CCO>[NH2:18][C@@H:7]([C@H:6]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)[OH:29])[CH2:8][N:9]([CH3:17])[C:10](=[O:11])[O:12][C:13]([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24654Hydrazine hydrate (1:1)HCID 59383055HCID 59383055, compound

Product 1

HCID 59382987HCID 59382987, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

2-((1S,2R)-1-cyclopentyl-1-hydroxy-3-(N-methyl-N-(t-butoxycarbonyl)amino)propan-2-yl)isoindoline-1,3-dione (0.7961 mg, 2.0 mmol) was dissolved in a minimal volume of EtOH (20 mL) and hydrazine monohydrate (0.5 mL, 10.3 mmol) was added. The solution was heated at 55° C. for 45 min and at reflux for 2 h. A white solid (precipitation of the hydrazone) resulted and the reaction was cooled to rt. Ether (50 mL) was added and the reaction was filtered through #1 Whatman filter paper. The filtrate was stripped and the residue was stirred in ether (15 mL) for 1 h, filtered, and stripped to give tert-butyl (2R,3S)-2-amino-3-cyclopentyl-3-hydroxypropyl-methylcarbamate (199.7 mg, 36%). LC-MS (3 min) tR=1.10 min, m/z=272 (M+).

Workup

  1. additionwas added
  2. temperatureat reflux for 2 h
  3. customA white solid (precipitation of the hydrazone)
  4. customresulted
  5. temperaturethe reaction was cooled to rt
  6. filtrationthe reaction was filtered through #1 Whatman
  7. filtrationfilter paper
  8. filtrationfiltered

Sources & evidence

ORD record
ord-5ae37286f05242a3b40ff25251bdd517
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

Loading…