cis-Phenylmethyl 5-{[(cyclopentyloxy)carbonyl]amino}-2-methyl-1-piperidinecarboxylate → Cis-cyclopentyl[6-methyl-3-piperidinyl]carbamate

HRID 2367439Notes

Reaction equation

HRID 2367439 reaction equation
[CH:1]1([O:6][C:7]([NH:9][C@H:10]2[CH2:15][N:14](C(OCC3C=CC=CC=3)=O)[C@@H:13]([CH3:26])[CH2:12][CH2:11]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.[Pd]>[CH:1]1([O:6][C:7](=[O:8])[NH:9][C@H:10]2[CH2:11][CH2:12][C@@H:13]([CH3:26])[NH:14][CH2:15]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 131731328cis-Phenylmethyl 5-{[(cyclopentyloxy)carbonyl]amino}-2-methyl-1-piperidinecarboxylate

Product 1

HCID 131731329Cis-cyclopentyl[6-methyl-3-piperidinyl]carbamateYield 106.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

cis-phenylmethyl 5-{[(cyclopentyloxy)carbonyl]amino}-2-methyl-1-piperidinecarboxylate (160 mg, 0.444 mmol) was dissolved in ethanol (3 mL) into a 25 mL RB flask. Pd/C (94 mg, 0.044 mmol) degussa type was added, and the resulting mixture was degassed with vacuum and charged with H2 in balloon. The reaction was stirred for 4 hours, and then filter through syringe filter. The filtrate was concentrated to afford the crude title compound (107 mg) as a clear oil. LC-MS (ES) m/z=227 [M+H]+.

Workup

  1. customthe resulting mixture was degassed with vacuum
  2. additioncharged with H2 in balloon
  3. filtrationfilter through syringe
  4. filtrationfilter
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2dbc87df6c4d4329940aee3faf03572b
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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