Potassium Carbonate → (3S)-tert-butyl 3-(3-hydroxy-5-methyl-3-phenylhex-5-enylamino)piperidine-1-carboxylate

HRID 884352Notes

Reaction equation

HRID 884352 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([OH:9])[CH2:5][C:6]([CH3:8])=[CH2:7].[NH2:16][C@H:17]1[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[OH:9][C:4]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH2:5][C:6]([CH3:8])=[CH2:7])[CH2:3][CH2:2][NH:16][C@H:17]1[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1501975tert-butyl (3S)-3-aminopiperidine-1-carboxylateHCID 595323881-Chlor-5-methyl-3-phenylhex-5-en-3-ol

Product 1

HCID 58278669(3S)-tert-butyl 3-(3-hydroxy-5-methyl-3-phenylhex-5-enylamino)piperidine-1-carboxylateYield 94.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-chloro-5-methyl-3-phenylhex-5-en-3-ol (5.16g, 23mmol), (S)-tert-butyl 3-aminopiperidine-1-carboxylate (6.9 g, 1.5 equiv), KI (4.0 g, 1.05 equiv), K2CO3 (4.77 g, 1.5 equiv) were mixed with acetonitrile (100 mL) and heated to reflux for 20 h. The mixture was filtered through a pad of Celite, concentrated and purified by chromatography on a 120 g silica gel column, eluted with a 0-10% methanol in CH2Cl2 gradient, to afford (3S)-tert-butyl 3-(3-hydroxy-5-methyl-3-phenylhex-5-enylamino)piperidine-1-carboxylate (8.41 g, 94% yield). LC-MS Method 1 tR=1.56 min., m/z 389 (M+1).

Workup

  1. temperatureheated
  2. temperatureto reflux for 20 h
  3. filtrationThe mixture was filtered through a pad of Celite
  4. concentrationconcentrated
  5. custompurified by chromatography on a 120 g silica gel column
  6. washeluted with a 0-10% methanol in CH2Cl2 gradient

Sources & evidence

ORD record
ord-38a9be6253544a768da081d8ee396bac
Source dataset
uspto-grants-2012_08
Patent number
US08242111B2

Reaction notes

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