Hydrochloric Acid → Hydroxy-di-thiophen-2-yl-acetic acid (1S,2R,4S,7S)-7-[(9-hydroxy-nonyl)-methyl-amino]-bicyclo[2.2.1]hept-2-yl ester

HRID 1670898Notes

Reaction equation

HRID 1670898 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]([CH3:39])[C@H:17]1[C@H:21]2[CH2:22][CH2:23][C@@H:18]1[C@H:19]([O:24][C:25](=[O:38])[C:26]([OH:37])([C:32]1[S:33][CH:34]=[CH:35][CH:36]=1)[C:27]1[S:28][CH:29]=[CH:30][CH:31]=1)[CH2:20]2)(C)(C)C.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[OH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]([CH3:39])[C@H:17]1[C@H:21]2[CH2:22][CH2:23][C@@H:18]1[C@H:19]([O:24][C:25](=[O:38])[C:26]([OH:37])([C:32]1[S:33][CH:34]=[CH:35][CH:36]=1)[C:27]1[S:28][CH:29]=[CH:30][CH:31]=1)[CH2:20]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 67349685Hydroxy-di-thiophen-2-yl-acetic acid (1S,2R,4S,7S)-7-{[9-(tert-butyldimethyl-silanyloxy)nonyl]methylamino}bicyclo[2.2.1]hept-2-ylester

Product 1

HCID 67349318Hydroxy-di-thiophen-2-yl-acetic acid (1S,2R,4S,7S)-7-[(9-hydroxy-nonyl)-methyl-amino]-bicyclo[2.2.1]hept-2-yl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of hydroxy-di-thiophen-2-yl-acetic acid (1S,2R,4S,7S)-7-{[9-(tert-butyl-dimethyl-silanyloxy)-nonyl]-methyl-amino}-bicyclo[2.2.1]hept-2-yl ester (0.51 g, 0.82 mmol) in THF (7 mL) was treated with 1 M HCl (3.5 mL) and stirred at RT for 45 min. The reaction mixture was neutralised with satd NaHCO3 (aq) and extracted with ethyl acetate. The combined organic layers were dried (Na2SO4), filtered, and concentrated to dryness to afford a light brown oil, which was used without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customto afford a light brown oil, which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-84e19e191d474972861914927ea02853
Source dataset
uspto-grants-2011_08
Patent number
US07994211B2

Reaction notes

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