Triethylamine → HCID 86700549, compound

HRID 2203141Notes

Reaction equation

HRID 2203141 reaction equation
[Si:1]([O:18][CH2:19][C@@H:20]1[CH2:25][CH2:24][CH2:23][CH:22]([OH:26])[N:21]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:34](N(CC)CC)C>CO.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[Si:1]([O:18][CH2:19][C@@H:20]1[CH2:25][CH2:24][CH2:23][CH:22]([O:26][CH3:34])[N:21]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 86700550HCID 86700550, compound

Product 1

HCID 86700549HCID 86700549, compoundYield 841.4%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 887MethanolSolvent

Procedure

To an ice cold solution of (2S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-6-hydroxypiperidine-1-carboxylate (2 g, 4.3 mmol) in methanol (20 mL) was added pyridinium p-toluenesulfonate (108 mg, 0.43 mmol). The reaction mixture was warmed to RT and stirred overnight. Triethylamine (87 mg, 0.86 mmol) was added, the reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (eluting with 0-15% EtOAc in petroleum ether), and combined with the product of three similar runs to provide the title intermediate (3.5 g).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (eluting with 0-15% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-52a2b9ebe07e4a01889e7af1f5a3b864
Source dataset
uspto-grants-2016_06
Patent number
US09365549B2

Reaction notes

Loading…