HCID 131714328, compound → HCID 131714327, compound

HRID 1719720Notes

Reaction equation

HRID 1719720 reaction equation
C([N:8]1[CH2:13][CH2:12][C@@H:11]([CH:14]([CH3:36])[CH2:15][O:16]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C@H:10]([O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[CH2:9]1)C1C=CC=CC=1>C(O)C.[Pd]>[Si:38]([O:37][C@H:10]1[C@H:11]([CH:14]([CH3:36])[CH2:15][OH:16])[CH2:12][CH2:13][NH:8][CH2:9]1)([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39]

Participants

4

Reactant 1

HCID 131714328HCID 131714328, compound

Product 1

HCID 131714327HCID 131714327, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Trans-1-benzyl-3-t-butyldimethylsilyloxy-4-(1-triphenylmethoxyprop-2-yl)piperidine (4.5 g; diastereomer A) was hydrogenated in ethanol (60 cm3) at 60° and 60 p.s.i. pressure over 10% palladium on carbon (0.9 g) for 5 hours. The solution was cooled, filtered through "Avicel" to remove the catalyst and evaporated in vacuo to afford trans-3-t-butyldimethylsilyloxy-4-(1-hydroxyprop-2-yl)piperidine as a crude oil (diastereomer A).

Workup

  1. temperatureThe solution was cooled
  2. filtrationfiltered through "Avicel"
  3. customto remove the catalyst
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-b6b9317ff0c449bb90bb0b0e453db3a6
Source dataset
uspto-grants-1985_09
Patent number
US04542132

Reaction notes

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