Ethyl 4-cyanooxane-4-carboxylate → HCID 53308467, compound

HRID 2047469Notes

Reaction equation

HRID 2047469 reaction equation
[C:1]([C:3]1([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2]>[Ni]>[NH2:2][CH2:1][C:3]1([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1

Participants

3

Reactant 1

HCID 22061355Ethyl 4-cyanooxane-4-carboxylate

Product 1

HCID 53308467HCID 53308467, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A mixture of the compound (8.09 g) obtained in step 1, Raney-nickel (containing water (50%), 5.18 g) washed with ethanol and ammonia (0.5% ethanol solution, 200 mL) was stirred under a hydrogen atmosphere (1 atm) at room temperature for 3 hr. The mixture was filtered, and concentrated under reduced pressure to give ethyl 4-(aminomethyl)tetrahydro-2H-pyran-4-carboxylate (6.79 g, 82%) as a yellow oil.

Workup

  1. washwashed with ethanol and ammonia (0.5% ethanol solution, 200 mL)
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-68215fd0e00242d6bf001193db82caaa
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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