Oxygen → HCID 10104276, compound

HRID 1492693Notes

Reaction equation

HRID 1492693 reaction equation
O=O.[CH:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]1[CH:15]=[C:14]([CH2:16][OH:17])[CH2:13][CH2:12][N:7]12>O1CCCC1>[CH:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]1[CH2:15][C@@H:14]([CH2:16][OH:17])[CH2:13][CH2:12][N:7]12

Participants

4

Reactant 2

HCID 977OxygenHCID 10878148HCID 10878148, compound

Product 1

HCID 10104276HCID 10104276, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The glass attachment of a 30 ml autoclave is charged in a glove box (oxygen content <1 ppm) with 0.20 g (1.0 mmol) of 6,7-dihydropyrido[1,2-a]indole-8-methanol, 9 ml of tetrahydrofuran and 1 ml of the above-mentioned catalyst solution. The hydrogenation is carried out at 80° C., an initial pressure of 60 bar of H2 and while stirring vigorously. After a hydrogenation time of 18 hours, the conversion is 99.9% according to GC. The pale yellow hydrogenation solution is evaporated. The residue is dissolved in diethyl ether and, in order to separate the catalyst, the solution is allowed to flow through a 5 g silica gel column. Rinsing of the column with diethyl ether, evaporation of the eluate and drying of the pale brown crystalline residue yields 0.20 g (100%) (S)-6,7,8,9-tetrahydropyrido[1,2-a]indole-8-methanol; GC 100 area %; 91.0% e.e.

Workup

  1. customis carried out at 80° C.
  2. customAfter a hydrogenation time of 18 hours
  3. customThe pale yellow hydrogenation solution is evaporated
  4. dissolutionThe residue is dissolved in diethyl ether and, in order
  5. customto separate the catalyst
  6. washRinsing of the column with diethyl ether, evaporation of the eluate and
  7. customdrying of the pale brown crystalline residue

Sources & evidence

ORD record
ord-faab25618d654e3abb3197f5b1f855ed
Source dataset
uspto-grants-1994_12
Patent number
US05374727

Reaction notes

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