Hydrochloric Acid → HCID 53799970, compound

HRID 2085913Notes

Reaction equation

HRID 2085913 reaction equation
CO[C:3]([CH:5]1[CH2:9][C:8](=[CH2:10])[CH2:7][CH:6]1[C:11]([OH:13])=[O:12])=O.C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+].Cl.[Na+].[Cl-]>C1COCC1>[CH2:10]=[C:8]1[CH2:7][C@H:6]2[C:11](=[O:12])[O:13][CH2:3][C@H:5]2[CH2:9]1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 14489541HCID 14489541, compound

Product 1

HCID 53799970HCID 53799970, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At −15° C., a solution of 2-methoxycarbonyl-4-methylidenecyclopentanecarboxylic acid (189.2 g; 1.027 mol) in THF (1 l ) was admixed with triethylamine (156.6 ml; 1.130 mol) and ethyl chloroformate (18.2 ml; 1.027 mol), and the reaction mixture was stirred at room temperature for 1 h. The precipitate was filtered off with suction and the filtrate was concentrated, taken up in methanol (1 l), NaBH4 (97.146 g; 2.568 mol) was added a little at a time at −15° C. and the mixture was stirred at room temperature for 1 h. For work-up, the mixture was admixed with 1 N HCl, saturated with NaCl and extracted with ethyl acetate. The combined organic phases were dried (Na2SO4) and concentrated, and the crude product was purified by chromatography.

Workup

  1. customAt −15° C.
  2. filtrationThe precipitate was filtered off with suction
  3. concentrationthe filtrate was concentrated
  4. stirringthe mixture was stirred at room temperature for 1 h
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic phases were dried (Na2SO4)
  7. concentrationconcentrated
  8. customthe crude product was purified by chromatography

Sources & evidence

ORD record
ord-4fedf65681284dbe8918cc0d744ced04
Source dataset
uspto-grants-2004_04
Patent number
US06723718B2

Reaction notes

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