HCID 86590764, compound → Carbamic acid, [2-[3-(3-pyridinyl)propoxy]ethyl]-, 1,1-dimethylethyl ester

HRID 1352593Notes

Reaction equation

HRID 1352593 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]#[C:8][CH2:9][O:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:2]=1>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH:2]=1

Participants

3

Reactant 1

HCID 86590764HCID 86590764, compound

Product 1

HCID 85898855Carbamic acid, [2-[3-(3-pyridinyl)propoxy]ethyl]-, 1,1-dimethylethyl esterYield 92.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under a nitrogen purge, 10% palladium on carbon (5.0 g) and 2-propanol (20 mL) were added to a pressure vessel. A solution of tert-butyl {2-[3-(pyridin-3-yl)prop-2-ynyloxy]ethyl}carbamate (22.7 g, 82.1 mmol) in methanol (200 mL) were then added. The vessel was purged three times with nitrogen and then placed under hydrogen pressure (50 psi, 3.4×105 Pa) for five hours. The reaction mixture was filtered through a layer of CELITE filter aid, and the filtrate was concentrated under reduced pressure to yield 21.3 g of tert-butyl {2-[3-(pyridin-3-yl)propoxy]ethyl}carbamate as a brown oil.

Workup

  1. customUnder a nitrogen purge
  2. addition10% palladium on carbon (5.0 g) and 2-propanol (20 mL) were added to a pressure vessel
  3. customThe vessel was purged three times with nitrogen
  4. customfor five hours
  5. filtrationThe reaction mixture was filtered through a layer of CELITE
  6. filtrationfilter aid
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8b0148613c7f464abeb38d4b07120001
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

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