Hydrochloric Acid → (R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochloride

HRID 1799600Notes

Reaction equation

HRID 1799600 reaction equation
[CH2:1]([O:8][C:9](=[O:25])[CH2:10][C@@H:11]([NH:17]C(OC(C)(C)C)=O)[C:12]([N:14]([CH3:16])[CH3:15])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:26]>>[ClH:26].[ClH:26].[CH2:1]([O:8][C:9](=[O:25])[CH2:10][C@@H:11]([NH2:17])[CH2:12][N:14]([CH3:15])[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 68990953(R)-3-tert-butoxycarbonylamino-N,N-dimethyl-succinamic acid benzyl ester

Product 1

HCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideYield 87%

Procedure

Borane-dimethyl sulfide complex (1.57 mL, 3.14 mmol) was added dropwise at 0° C. to a solution of (R)-3-tert-butoxycarbonylamino-N,N-dimethyl-succinamic acid benzyl ester (500 mg, 1.43 mmol). The reaction mixture was warmed to room temperature and heated at reflux for 3 hours, then cooled to 0° C. and treated dropwise with 6 M aq. hydrochloric acid solution (0.68 mL, 4.1 mmol). The reaction mixture was allowed to warm to room temperature and concentrated in vacuo. Residual water was azeotroped with toluene and concentrated under high vacuum to afford (R)-3-amino-4-dimethylamino-butyric acid benzyl ester dihydrochloride (384 mg, 87%). White solid, m/e=237.4 ([M+H]+).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. temperaturecooled to 0° C.
  4. temperatureto warm to room temperature
  5. concentrationconcentrated in vacuo
  6. customResidual water was azeotroped with toluene
  7. concentrationconcentrated under high vacuum

Sources & evidence

ORD record
ord-309ea0d1481d4133ae5e8b4f3afc7978
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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