Triethylamine → (3S,5S,6R,8S)-8-Allyl-6-(3-chlorophenyl)-5-(4-chlorophenyl)-3,8-diethyl-2,3,5,6,7,8-hexahydrooxazolo[3,2-a]pyridin-4-ium methanesulfonate

HRID 1048552Notes

Reaction equation

HRID 1048552 reaction equation
[CH2:1]([C:4]1([CH2:30][CH3:31])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH2:27][CH3:28])[CH2:25][OH:26])[C:5]1=O)[CH:2]=[CH2:3].C(N(CC)CC)C.[CH3:39][S:40]([O:43]S(C)(=O)=O)(=[O:42])=[O:41]>C(Cl)Cl>[CH3:39][S:40]([O-:43])(=[O:42])=[O:41].[CH2:1]([C@@:4]1([CH2:30][CH3:31])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N+:6]2[C@@H:24]([CH2:27][CH3:28])[CH2:25][O:26][C:5]1=2)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 67998816(5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-ethyl-1-((S)-1-hydroxybutan-2-yl)piperidin-2-one

Product 1

HCID 86660742(3S,5S,6R,8S)-8-Allyl-6-(3-chlorophenyl)-5-(4-chlorophenyl)-3,8-diethyl-2,3,5,6,7,8-hexahydrooxazolo[3,2-a]pyridin-4-ium methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-ethyl-1-((S)-1-hydroxybutan-2-yl)piperidin-2-one (300 mg, 0.652 mmol) (Example 202, Step B) in DCM (6 mL) was added triethylamine (270 μl, 1.955 mmol) and methanesulfonic anhydride (170 mg, 0.977 mmol) successively at 0° C. The reaction was allowed to warm to rt. After being stirred at rt for 2 h, the reaction was quenched with 10% aq. citric acid, extracted with DCM and the combined extracts were washed with water, dried over Na2SO4, filtered and the filtrate was and concentrated to give the title compound.

Workup

  1. customthe reaction was quenched with 10% aq. citric acid
  2. extractionextracted with DCM
  3. washthe combined extracts were washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-917655d8cf25495bbdf9dc4f7961a230
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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