Ethyl 1-benzyl-4-(cyanomethyl)-3-oxopiperidine-4-carboxylate → Ethyl 4-(2-aminoethyl)-1-benzyl-3-hydroxypiperidine-4-carboxylate

HRID 1848526Notes

Reaction equation

HRID 1848526 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:19][C:20]#[N:21])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10](=[O:22])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.CO.[Pt]=O>[NH2:21][CH2:20][CH2:19][C:11]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH:10]1[OH:22]

Participants

4

Reactant 1

HCID 86709485Ethyl 1-benzyl-4-(cyanomethyl)-3-oxopiperidine-4-carboxylate

Product 1

HCID 86709519Ethyl 4-(2-aminoethyl)-1-benzyl-3-hydroxypiperidine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 10129899Acetic acid methanolSolvent

Procedure

Into a 10000-mL 4-necked round-bottom flask was placed a solution of ethyl 1-benzyl-4-(cyanomethyl)-3-oxopiperidine-4-carboxylate (180 g, 599.30 mmol) in acetic acid/methanol (1:1, 5.4 L) and platinum oxide (27 g, 118.90 mmol). The flask was then flushed and charged with hydrogen and stirred overnight at room temperature. After filtration under nitrogen through CELITE®, the filtrate was concentrated under vacuum to give the title compound.

Workup

  1. customInto a 10000-mL 4-necked round-bottom flask was placed
  2. customThe flask was then flushed
  3. additioncharged with hydrogen
  4. filtrationAfter filtration under nitrogen through CELITE®
  5. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-d048d3a0bf6b4518b59702acecd54f74
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

Loading…