Hydrochloric Acid → HCID 70025388, compound

HRID 1368181Notes

Reaction equation

HRID 1368181 reaction equation
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)[O:4]1.[CH3:10][C@@H:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl.[CH2:20]([C:27](O)=O)[C:21](CC(O)=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>Cl.O>[C:12]1([CH:11]([N:18]2[CH:6]3[CH2:5][CH2:27][C@@H:20]2[CH2:21][C:3](=[O:4])[CH2:7]3)[CH3:10])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 68328Acetonedicarboxylic acidHCID 790982,5-DimethoxytetrahydrofuranHCID 6431891-Phenethylamine, (+)-

Product 1

HCID 70025388HCID 70025388, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent2×

Procedure

Three drops of 5M hydrochloric acid were added to a mixture of 2,5-dimethoxytetrahydrofuran (16.5 g) and water (70 ml). A cooled mixture of (R)-a-methylbenzylamine (15.125 g) and 5M hydrochloric acid (30 ml) was then added followed by 1,3-acetonedicarboxylic acid (18.26 g) sodium acetate (10 g) and water (100 ml). After 5 days the mixture was basified with aqueous sodium carbonate solution and extracted with ethyl acetate. The extracts were washed with brine, dried (MgSO4) and evaporated under reduced pressure. Chromatography [SiO2; ethyl acetate:hexane (10:90) to (20:80)] gave (R)-8-(1-phenylethyl)-8-azabicyclo[3.2.1]octan-3-one.

Workup

  1. additionwas then added
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-cc1d089dc97a47d9a8a79ca4edc059d1
Source dataset
uspto-grants-2003_06
Patent number
US06573275B1

Reaction notes

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