1-Butanol → HCID 58092718, compound

HRID 1430142Notes

Reaction equation

HRID 1430142 reaction equation
Cl.Cl.Cl.[CH3:4][O:5][C:6]([C@@H:8]1[CH2:12][C@H:11]([N:13]([CH3:15])[CH3:14])[CH2:10][NH:9]1)=[O:7].[CH2:16](O)[CH2:17][CH2:18]C>>[CH2:4]([O:5][C:6]([C@@H:8]1[CH2:12][C@H:11]([N:13]([CH3:14])[CH3:15])[CH2:10][NH:9]1)=[O:7])[CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 3

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 66891172HCID 66891172, compound

Product 1

HCID 58092718HCID 58092718, compound

Conditions

Temperature
115 °C

Procedure

Concentrated hydrochloric acid (0.3 ml) is added to a mixture of (2S,4S)-4-dimethylamino-pyrrolidine-2-carboxylic acid methyl ester dihydrochloride (400 mg) and 1-butanol (4 ml) and heated for 18 hours at 115° C. After cooling the reaction mixture is evaporated then partitioned between dicloromethane and aqueous sodium bicarbonate solution and the dichloromethane layers dried and evaporated to give the title compound as a brown oil which is used without further purification.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. customis evaporated
  3. customthen partitioned between dicloromethane and aqueous sodium bicarbonate solution
  4. dry with materialthe dichloromethane layers dried
  5. customevaporated

Sources & evidence

ORD record
ord-cb5ce0d716554f3481c956da00971929
Source dataset
uspto-grants-2015_01
Patent number
US08940771B2

Reaction notes

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