HCID 19697615, compound → HCID 19697660, compound

HRID 863241Notes

Reaction equation

HRID 863241 reaction equation
C([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH:10]([CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:9]1)C1C=CC=CC=1>O1CCCC1.[Pd]>[Si:20]([O:19][CH2:18][CH:10]1[CH2:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:8][CH2:9]1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

4

Reactant 1

HCID 19697615HCID 19697615, compound

Product 1

HCID 19697660HCID 19697660, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

25.2 g of 1-benzyl-3(R,S)-(tert-butyldimethylsilyloxymethyl)-1,2,3,4-tetrahydroquinoline in 250 ml of tetrahydrofuran are hydrogenated in the presence of 2.0 g of 10% palladium-on-charcoal under customary reaction conditions. Purification of the crude product over 500 g of silica gel with a 1:1 mixture of methylene chloride and hexane as the solvent gives 7.6 g of the title compound: Rf (1:1 mixture of methylene chloride and hexane)=0.19.

Workup

  1. customPurification of the crude product over 500 g of silica gel
  2. additionwith a 1:1 mixture of methylene chloride and hexane as the solvent

Sources & evidence

ORD record
ord-c046883ad8f4444aad10e2572902af5b
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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