Hydrochloric Acid → HCID 15485234, compound

HRID 1872749Notes

Reaction equation

HRID 1872749 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][C@@H:8]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:9][N:10]1[CH2:15][CH2:14][C:13](O)([C:16]2[S:17][CH:18]=[CH:19][C:20]=2[O:21][CH3:22])[CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].Cl>O1CCCC1>[C:1]([O:5][C:6](=[O:31])[NH:7][C@@H:8]([CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:9][N:10]1[CH2:11][CH:12]=[C:13]([C:16]2[S:17][CH:18]=[CH:19][C:20]=2[O:21][CH3:22])[CH2:14][CH2:15]1)([CH3:4])([CH3:2])[CH3:3].[CH2:24]([C@H:8]([NH2:7])[CH2:9][N:10]1[CH2:11][CH:12]=[C:13]([C:16]2[S:17][CH:18]=[CH:19][C:20]=2[O:21][CH3:22])[CH2:14][CH2:15]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 15485233HCID 15485233, compound

Product 2

HCID 15485234HCID 15485234, compoundHCID 54080600HCID 54080600, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.2 g (5 mmol) (S)-{1-benzyl-2-[4-hydroxy-4-(3-methoxy-thiophen-2-yl)-piperidin-1-yl]-ethyl}-carbamic acid tert-butyl ester in 20 mL tetrahydrofuran was treated at once with 20 mL 3M hydrochloric acid. The reaction mixture was stirred at ambient temperature overnight and then extracted with 50 mL diethyl ether. The remaining aqueous layer was basefied with sodium bicarbonate powder and extracted with chloroform (3×60 mL). The combined organic extract was dried over magnesium sulfate, filtered and evaporated to dryness in vacuo. The residue was flash chromatographed on 60 g silica gel. Elution with 2% methanol in chloroform yielded both, 100 mg of the title compound as a yellowish oil and 700 mg of (1S)-1-benzyl-2-[4-(3-methoxy-thiophen-2-yl)-3,6-dihydro-2H-pyridin-1-yl]-ethylamine as an amber oil.

Workup

  1. extractionextracted with 50 mL diethyl ether
  2. extractionextracted with chloroform (3×60 mL)
  3. extractionThe combined organic extract
  4. dry with materialwas dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness in vacuo
  7. customchromatographed on 60 g silica gel
  8. washElution with 2% methanol in chloroform

Sources & evidence

ORD record
ord-00af655a65234088a41f609f7293fe92
Source dataset
uspto-grants-2000_08
Patent number
US06110943

Reaction notes

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