Water → HCID 53779442, compound

HRID 1977045Notes

Reaction equation

HRID 1977045 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]2[CH2:14][C@H:15]([CH2:18][N:19]3[C:27]4[C:22](=[CH:23][C:24]([F:28])=[CH:25][CH:26]=4)[CH:21]=[CH:20]3)[CH2:16][CH2:17][C@H:10]2[CH2:9]1)(OC(C)(C)C)=O.O>FC(F)(F)C(O)=O>[F:28][C:24]1[CH:23]=[C:22]2[C:27](=[CH:26][CH:25]=1)[N:19]([CH2:18][C@H:15]1[CH2:14][N:11]3[CH2:12][CH2:13][NH:8][CH2:9][C@@H:10]3[CH2:17][CH2:16]1)[CH:20]=[CH:21]2

Participants

4

Reactant 2

HCID 962WaterHCID 22940601HCID 22940601, compound

Product 1

HCID 53779442HCID 53779442, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3.0 g (7.75 mmol) of (7R,9aS)-2-BOC-7-(5-fluoroindol-1-yl)methyl-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine in 200 mL of 70:30 trifluoroacetic acid:water was stirred at room temperature for 1 h. The mixture was concentrated in vacuo, basified with 15% sodium hydroxide and extracted with ethyl acetate (2×). The combined organics were dried (magnesium sulfate), filtered and evaporated to give 2.0 g (90%) of (7R,9aS)-7-(5-fluoroindol-1-yl)methyl-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionextracted with ethyl acetate (2×)
  3. dry with materialThe combined organics were dried (magnesium sulfate)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-7cfde53c512a47f2b0e60222b6a14a1e
Source dataset
uspto-grants-2001_05
Patent number
US06231833B1

Reaction notes

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