Benzyl trans(+/-)-4-[(tert-butoxycarbonyl)amino]-3-{[tert-butyl(dimethyl)silyl]oxy}piperidine-1-carboxylate → tert-Butyl (trans(+/-)-3-{[tert-butyl(dimethyl)silyl]oxy}piperidin-4-yl)carbamate

HRID 1430813Notes

Reaction equation

HRID 1430813 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][N:12](C(OCC2C=CC=CC=2)=O)[CH2:11][C@H:10]1[O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[Si:26]([O:25][C@H:10]1[C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:14][CH2:13][NH:12][CH2:11]1)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]

Participants

4

Reactant 1

HCID 60200764Benzyl trans(+/-)-4-[(tert-butoxycarbonyl)amino]-3-{[tert-butyl(dimethyl)silyl]oxy}piperidine-1-carboxylate

Product 1

HCID 60200917tert-Butyl (trans(+/-)-3-{[tert-butyl(dimethyl)silyl]oxy}piperidin-4-yl)carbamateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (+/−)-(3R,4R)-benzyl 4-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)piperidine-1-carboxylate (13 g, 28.0 mmol) and Pd/C (5% on carbon, 1.786 g, 0.839 mmol) in methanol (250 mL) was hydrogenated at 30 psi overnight. The mixture was filtered through Celite and the filtrate was concentrated in vacuo and further dried under high vacuum at 40° C. overnight. The crude product was used without purification. (+/−)-tert-butyl ((3R,4R)-3-((tert-butyldimethylsilyl)oxy)piperidin-4-yl)carbamate (8.8 g, 26.6 mmol, 95% yield) was obtained as a white solid.

Workup

  1. customwas hydrogenated at 30 psi overnight
  2. filtrationThe mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customfurther dried under high vacuum at 40° C. overnight
  5. customThe crude product was used without purification

Sources & evidence

ORD record
ord-c235ee6d722841838ed611ea6b6fe686
Source dataset
uspto-grants-2015_01
Patent number
US08940736B2

Reaction notes

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