(2S,3R)-1-tert-Butoxycarbonyl-3-(3-hydroxypropyn-1-yl)-2-phenylpiperidin-3-ol → Z-(2S,3R)-1-tert-Butoxycarbonyl-3-(3-hydroxyprop-1-en-1-yl)-2-phenylpiperidin-3-ol

HRID 1420847Notes

Reaction equation

HRID 1420847 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@:10]([C:15]#[C:16][CH2:17][OH:18])([OH:14])[C@@H:9]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@:10](/[CH:15]=[CH:16]\[CH2:17][OH:18])([OH:14])[C@@H:9]1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 11301992(2S,3R)-1-tert-Butoxycarbonyl-3-(3-hydroxypropyn-1-yl)-2-phenylpiperidin-3-ol

Product 1

HCID 59038479Z-(2S,3R)-1-tert-Butoxycarbonyl-3-(3-hydroxyprop-1-en-1-yl)-2-phenylpiperidin-3-olYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 131709914Lindlars catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Palladium on calcium carbonate, poisoned with lead (Lindlar catalyst, 2 g) was added to a solution of (2S,3R)-1-tert-butoxycarbonyl-3-(3-hydroxypropyn-1yl)-2-phenylpiperidin-3-ol (Description 7; 32 g, 96.6 mmol) in ethyl acetate (300 mL) and the mixture was stirred under hydrogen (1 Atm.) for 4 h. The mixture was filtered and the solvent was evaporated under reduced pressure to give the title compound as an oil (32 g, 100%). 1H NMR (360 MHz, CDCl3) δ7.42 (2 H, d, J 7.6 Hz), 7.35-7.25 (3 H, m), 5.83 (1 H, d, J 12.3 Hz), 5.68 (1 H, dt, J 12.3, 6.0 Hz), 5.06 (1 H, s), 4.27 (1 H, m), 4.12 (2 H, m), 3.32 (1 H, m), 3.13 (1 H, s), 2.28 (1 H, t, J 5.9 Hz), 2.02 (1 H, m), 1.92-1.78 (3 H, m), and 1.32 (9 H, s). m/z (ES+) 334 (M+1).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b18b3c3aab5647fe935b852e6bbfc5c0
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

Loading…