Hydrochloric Acid → (1S,2R,3S)-3-amino-1-cyclopropyl-4-phenyl-1,2-butanediol

HRID 275629Notes

Reaction equation

HRID 275629 reaction equation
[CH2:1]([C@H:8]([NH:16]C(=O)OC(C)(C)C)[C@@H:9]([OH:15])[C@H:10]([CH:12]1[CH2:14][CH2:13]1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>CO>[NH2:16][C@@H:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@@H:9]([OH:15])[C@H:10]([CH:12]1[CH2:13][CH2:14]1)[OH:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 56984559tert-butyl [(1S,2R,3S)-1-benzyl-3-cyclopropyl-2,3-dihydroxypropyl]carbamate

Product 1

HCID 22861541(1S,2R,3S)-3-amino-1-cyclopropyl-4-phenyl-1,2-butanediolYield 50.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.0 g (6.23 mmol) of tert-butyl [(1S,2R,3S)-1-benzyl-3-cyclopropyl-2,3-dihydroxypropyl]carbamate in 20 ml of methanol was treated with 20 ml of 2N hydrochloric acid and the solution was heated to 500 for 90 minutes. After cooling, the solution was neutralized by the addition of 40 ml of 1N sodium hydroxide solution and evaporated to dryness on a rotary evaporator under reduced pressure. The residue was partitioned between water and methylene chloride. The organic phase was washed with water and saturated sodium chloride solution, dried over magnesium sulphate, filtered and evaporated under reduced pressure. There was obtained 0.7 g of (1S,2R,3S)-3-amino-1-cyclopropyl-4-phenyl-1,2-butanediol as white crystalline solid, MS: 150 (M-C4H8O)+.

Workup

  1. temperaturethe solution was heated to 500 for 90 minutes
  2. temperatureAfter cooling
  3. customevaporated to dryness on a rotary evaporator under reduced pressure
  4. customThe residue was partitioned between water and methylene chloride
  5. washThe organic phase was washed with water and saturated sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-982c17f1fbf74fc28e242e87b129b486
Source dataset
uspto-grants-1995_02
Patent number
US05393875

Reaction notes

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