HCID 131734940, compound → Tert-butyl (2-chloro-5-cyano-3-(4-hydroxybutan-2-yl)phenyl)carbamate

HRID 921851Notes

Reaction equation

HRID 921851 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([CH2:10][CH2:11][OH:12])=[CH2:9])=[CH:6][C:5]([C:13]#[N:14])=[CH:4][C:3]=1[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19]>CCO.[Pt](=O)=O>[Cl:1][C:2]1[C:7]([CH:8]([CH2:10][CH2:11][OH:12])[CH3:9])=[CH:6][C:5]([C:13]#[N:14])=[CH:4][C:3]=1[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19]

Participants

4

Reactant 1

HCID 131734940HCID 131734940, compound

Product 1

HCID 131734941Tert-butyl (2-chloro-5-cyano-3-(4-hydroxybutan-2-yl)phenyl)carbamateYield 58.8%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

Tert-butyl (2-chloro-5-cyano-3-(4-hydroxybut-1-en-2-yl)phenyl)carbamate (272 mg, 0.843 mmol) was taken up in EtOH (8 mL) and the flask was evacuated and filled with N2 3×. Next, platinum (IV) oxide (19.14 mg, 0.084 mmol) was added, and the flask was purged again. The reaction was stirred under 1 atm hydrogen at room temperature for 3 h. The reaction was monitored by TLC. The reaction mixture was filtered through celite, rinsing with MeOH. The solvent was removed in vacuo and the material was purified by flash column chromatography (0-40% EtOAc/Hex; 40 g column). Tert-butyl (2-chloro-5-cyano-3-(4-hydroxybutan-2-yl)phenyl)carbamate (161 mg) was obtained as a colorless glassy liquid.

Workup

  1. customthe flask was evacuated
  2. additionfilled with N2 3×
  3. customthe flask was purged again
  4. filtrationThe reaction mixture was filtered through celite
  5. washrinsing with MeOH
  6. customThe solvent was removed in vacuo
  7. customthe material was purified by flash column chromatography (0-40% EtOAc/Hex; 40 g column)

Sources & evidence

ORD record
ord-5bb45b4b636d4fca84026740021936fe
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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