Triethylamine → (R)-3-(Boc-amino)-1-phenyl-piperidine

HRID 1467309Notes

Reaction equation

HRID 1467309 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:15]1([N:11]2[CH2:12][CH2:13][CH2:14][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:10]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 1514172(3R)-3-Aminopiperidine, 3-BOC protected

Product 1

HCID 70652814(R)-3-(Boc-amino)-1-phenyl-piperidine

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-3-(tert-butoxycarbonylamino)piperidine (0.10 g, 0.50 mmol), phenylboronic acid (0.13 g, 1.1 mmol) and copper (II) acetate (0.10 g, 0.551 mmol) in DCM (2 ml) under air was charged with triethylamine (0.14 ml, 1.0 mmol), sealed and stirred at RT for 18 hours followed by stirring at 60° C. for 72 hours. The reaction mixture was filtered through celite and eluted with DCM/MeOH. The filtrate was concentrated in vacuo and purified by flash chromatography (Biotage, 0-20% MeOH/DCM) to provide tert-butyl [(3R)-1-phenylpiperidin-3-yl]carbamate.

Workup

  1. customsealed
  2. stirringby stirring at 60° C. for 72 hours
  3. filtrationThe reaction mixture was filtered through celite
  4. washeluted with DCM/MeOH
  5. concentrationThe filtrate was concentrated in vacuo
  6. custompurified by flash chromatography (Biotage, 0-20% MeOH/DCM)

Sources & evidence

ORD record
ord-116c3402f661478d818bd8f9ee383ede
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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