Diisopropylethylamine → (S)-1-(6-Iodo-3-methanesulfonyl-2-methyl-quinolin-4-yl)-piperidin-3-ol

HRID 13665Notes

Reaction equation

HRID 13665 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]=[C:4]([CH3:13])[C:3]=1[S:14]([CH3:17])(=[O:16])=[O:15].[OH:18][C@H:19]1[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[I:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[C:4]([CH3:13])[C:3]([S:14]([CH3:17])(=[O:16])=[O:15])=[C:2]2[N:21]1[CH2:22][CH2:23][CH2:24][C@H:19]([OH:18])[CH2:20]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6950221(S)-3-HydroxypiperidineHCID 120016244-Chloro-6-iodo-3-methanesulfonyl-2-methyl-quinoline

Product 1

HCID 12001809(S)-1-(6-Iodo-3-methanesulfonyl-2-methyl-quinolin-4-yl)-piperidin-3-olYield 54.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-6-iodo-3-methanesulfonyl-2-methyl-quinoline (compound of example D.2) (300 mg, 0.786 mmol), (S)-(+)-3-hydroxypiperidine (119 mg, 0.865 mmol) and N,N-diisopropyl ethyl amine (0.148 mL, 0.865 mmol) were heated in dry N,N-dimethylformamide (3 mL) for 0.5 h at 100° C. N,N-Dimethylformamide was evaporated at 40° C./0.1 mbar, the residue was extraced with dichloromethane and 10% Na2CO3, and then purified by chromatography on silica gel in dichloromethane/methanol 20:1. One obtained a yellow oil which was triturated with ethyl acetate, and the resulting white crystals were filtered off. One obtained 191 mg (54%) of white crystals. MS: m/z=447 (M+H).

Workup

  1. customN,N-Dimethylformamide was evaporated at 40° C./0.1 mbar
  2. custompurified by chromatography on silica gel in dichloromethane/methanol 20:1
  3. customOne obtained a yellow oil which
  4. customwas triturated with ethyl acetate
  5. filtrationthe resulting white crystals were filtered off

Sources & evidence

ORD record
ord-704abc9b5c6245dbbb90c7372e439fa7
Source dataset
uspto-grants-2010_06
Patent number
US07728142B2

Reaction notes

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