Ethyl Acetate → HCID 68542650, compound

HRID 661486Notes

Reaction equation

HRID 661486 reaction equation
[CH:1]1([NH:4][CH2:5][C@H:6]2[C@@H:10]([F:11])[CH2:9][NH:8][CH2:7]2)[CH2:3][CH2:2]1.[ClH:12].CO.C(OCC)(=O)C>CO>[ClH:12].[ClH:12].[CH:1]1([NH:4][CH2:5][C@H:6]2[C@@H:10]([F:11])[CH2:9][NH:8][CH2:7]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8857Ethyl Acetate2×HCID 21893726Hydrochloride methanolHCID 59171047HCID 59171047, compound

Product 1

HCID 68542650HCID 68542650, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (3S,4R)-3-cyclopropylaminomethyl-4-fluoropyrrolidine (4.74 g, 30.0 mmol) in 15 mL of methanol, 60.0 mL of a 10% hydrogen chloride-methanol solution was added dropwise over 10 minutes under stirring at room temperature. The mixture was stirred for 5 minutes. 75 mL of ethyl acetate was then added dropwise over 10 minutes and the mixture was further stirred for 10 minutes. 50 mL of ethylacetate was further added dropwise over 10 minutes and the mixture was further stirred for 30 minutes. The resulting crystals were collected by filtration and washed with 100 mL of ethyl acetate. The washed product was dried at 50° C. under reduced pressure for 4 hours to give 4.98 g of the title compound as a faint brown crystalline powder (72% yield).

Workup

  1. stirringThe mixture was stirred for 5 minutes
  2. stirringthe mixture was further stirred for 10 minutes
  3. stirringthe mixture was further stirred for 30 minutes
  4. filtrationThe resulting crystals were collected by filtration
  5. washwashed with 100 mL of ethyl acetate
  6. customThe washed product was dried at 50° C. under reduced pressure for 4 hours

Sources & evidence

ORD record
ord-e6c0e1885e0041d4ae0f71bf611d981c
Source dataset
uspto-grants-2011_12
Patent number
US08084622B2

Reaction notes

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