HCID 22940600, compound → HCID 53849828, compound

HRID 1977058Notes

Reaction equation

HRID 1977058 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]2[CH2:14][C@H:15]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:16][CH2:17][C@H:10]2[CH2:9]1)(OC(C)(C)C)=O>FC(F)(F)C(O)=O.O>[F:26][C:23]1[CH:22]=[CH:21][C:20]([O:19][CH2:18][C@H:15]2[CH2:14][N:11]3[CH2:12][CH2:13][NH:8][CH2:9][C@@H:10]3[CH2:17][CH2:16]2)=[CH:25][CH:24]=1

Participants

4

Reactant 1

HCID 22940600HCID 22940600, compound

Product 1

HCID 53849828HCID 53849828, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 44.4 g (122 mmol) of (7R,9aS)-2-BOC-7-(4-fluorophenoxy)methyl-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine (Preparation 7) in 500 mL of trifluroacetic acid and 200 mL of water was stirred at room temperature for 16 h. The mixture was concentrated by evaporation, the residue dissolved in water, basified with 15% NaOH, and extracted with ethyl acetate (2×). The organic layers were dried (magnesium sulfate), filtered and evaporated to give 31.4 g (96%) of (7R,9aS)-7-(4-fluorophenoxy)methyl-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine which was suitable for use in subsequent reactions. Purification of a 0.40 g sample by flash silica gel chromatography eluting with 90:10 chloroform:methanol gave 0.38 g of colorless crystals. mp (−2 HCl) 200-201° C. 13C NMR (base, CDCl3): δ27.2, 29.1, 36.3, 45.9, 51.9, 56.0, 59.1, 62.5, 71.7, 115.4 (d, JCF=8), 115.7 (d, JCF=23). HRMS calcd for C15H21FN2O: 264.1638, found: 264.1660.

Workup

  1. concentrationThe mixture was concentrated by evaporation
  2. dissolutionthe residue dissolved in water
  3. extractionextracted with ethyl acetate (2×)
  4. dry with materialThe organic layers were dried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-a22b9d5cae4d4f8894657e9e7e2f37f0
Source dataset
uspto-grants-2001_05
Patent number
US06231833B1

Reaction notes

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