Methanol → methyl (2R,4S)-4-hydroxypiperidine-2-carboxylate

HRID 2185436Notes

Reaction equation

HRID 2185436 reaction equation
C1([C@@H]([N:9]2[CH2:15][CH2:14][C@@H:13]3[CH2:16][C@H:10]2[C:11](=[O:17])[O:12]3)C)C=CC=CC=1.[CH3:18][OH:19]>[Pd]>[CH3:18][O:19][C:11](=[O:17])[C@H:10]1[CH2:16][C@@H:13]([OH:12])[CH2:14][CH2:15][NH:9]1

Participants

4

Reactant 2

HCID 887MethanolHCID 10823407(1S,5R)-2-[(1S)-1-phenylethyl]-6-oxa-2-azabicyclo[3.2.1]octan-7-one

Product 1

HCID 11321108methyl (2R,4S)-4-hydroxypiperidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of (1S,5R)-2-((S)-1-phenylethyl)-6-oxa-2-azabicyclo[3.2.1]octan-7-one (2.95 g) and 10% palladium on activated carbon (570 mg) in methanol (75 mL) was stirred at room temperature for 6 hr under hydrogen (3.5 kgf/cm2). The catalysts were removed by filtration and washed with methanol. The combined organic layers were evaporated in vacuo. A mixture of the residue and 10% palladium on activated carbon (500 mg) in methanol (75 mL) was stirred at room temperature for 8 hr under hydrogen (3.5 kgf/cm2). The catalysts were removed by filtration and washed with methanol. The combined organic layers were evaporated in vacuo. The mixture of the residue and 10% palladium on activated carbon (504 mg) in methanol (75 mL) was stirred at room temperature for 8 hr under hydrogen (4.0 kgf/cm2). The catalysts were removed by filtration and washed with methanol. The combined organic layers were evaporated in vacuo to give the title compound (2.11 g): 1H NMR (400 MHz, CDCl3) δ 1.32-1.49 (m, 2H), 1.83 (br s, 2H), 1.93-1.95 (m, 1H), 2.27-2.32 (m, 1H), 2.61-2.69 (m, 1H), 3.22 (dt, J=12.7, 3.9 Hz, 1H), 3.39 (dd, J=2.9, 10.7 Hz, 1H), 3.71-3.78 (m, 1H), and 3.75 (m, 3H).

Workup

  1. customThe catalysts were removed by filtration
  2. washwashed with methanol
  3. customThe combined organic layers were evaporated in vacuo
  4. additionA mixture of the residue and 10% palladium on activated carbon (500 mg) in methanol (75 mL)
  5. stirringwas stirred at room temperature for 8 hr under hydrogen (3.5 kgf/cm2)
  6. customThe catalysts were removed by filtration
  7. washwashed with methanol
  8. customThe combined organic layers were evaporated in vacuo
  9. additionThe mixture of the residue and 10% palladium on activated carbon (504 mg) in methanol (75 mL)
  10. stirringwas stirred at room temperature for 8 hr under hydrogen (4.0 kgf/cm2)
  11. customThe catalysts were removed by filtration
  12. washwashed with methanol
  13. customThe combined organic layers were evaporated in vacuo

Sources & evidence

ORD record
ord-2b74b0b6790a48f9a8be37f807a46715
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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