Ethanol → HCID 59201362, compound

HRID 451755Notes

Reaction equation

HRID 451755 reaction equation
[CH:1]1([C@H:7]([OH:30])[C@H:8]([N:19]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:9][N:10]([CH3:18])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCO.O.NN>CCOCC>[NH2:19][C@@H:8]([C@H:7]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[OH:30])[CH2:9][N:10]([CH3:18])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 59201739HCID 59201739, compound

Product 1

HCID 59201362HCID 59201362, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
55 °C

Procedure

tert-butyl (2R,3S)-3-cyclohexyl-2-(1,3-dioxoisoindolin-2-yl)-3-hydroxypropyl(methyl)carbamate (500 mg, 1.20 mmol) was dissolved into a minimal volume of EtOH (12 mL) and hydrazine monohydrate (85% in EtOH, 0.35 mL, 6.00 mmol) was added. The solution was heated at 55° C. for 45 min and then the reaction temperature was raised to reflux for 2 h. A white solid formed. The reaction was cooled to rt, Et2O (50 mL) was added and the reaction was filtered. The filtrate was stripped and the residue was stirred in Et2O (15 mL) for 1 h and filtered. The filtrate was stripped to afford tert-butyl (2R,3S)-2-amino-3-cyclohexyl-3-hydroxypropyl(methyl)carbamate (300 mg, yield 87%), which was pure enough to use directly in the next step. MS (E/Z): 287 (M+H+).

Workup

  1. additionwas added
  2. temperaturethe reaction temperature was raised
  3. temperatureto reflux for 2 h
  4. customA white solid formed
  5. temperatureThe reaction was cooled to rt
  6. filtrationthe reaction was filtered
  7. filtrationfiltered

Sources & evidence

ORD record
ord-cc81ad6f784e466abc8ce7c4a26ecf0a
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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