HCID 86640829, compound → HCID 59279578, compound

HRID 1675764Notes

Reaction equation

HRID 1675764 reaction equation
C([O:5][C:6](=[O:27])[CH2:7][N:8]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:10]2([CH2:15][CH2:14][N:13]([CH2:16][C:17]([F:20])([F:19])[F:18])[CH2:12][CH2:11]2)[CH2:9]1)(C)(C)C>C(Cl)Cl.C(C(O)=O)(F)(F)F>[F:19][C:17]([F:18])([F:20])[CH2:16][N:13]1[CH2:14][CH2:15][C:10]2([C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:8]([CH2:7][C:6]([OH:27])=[O:5])[CH2:9]2)[CH2:11][CH2:12]1

Participants

4

Reactant 1

HCID 86640829HCID 86640829, compound

Product 1

HCID 59279578HCID 59279578, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent2×

Procedure

A solution of tert-butyl[1′-(2,2,2-trifluoroethyl)spiro[indole-3,4′-piperidin]-1(2H)-yl]acetate (91.0 mg, 0.237 mmol) from Step B in CH2Cl2 (2 mL) and CF3CO2H (1 mL) was stirred at ambient temperature for 6 h. Added CF3CO2H (1 mL) and stirred 1 additional hour. The mixture was concentrated in vacuo. The crude product was partitioned between CH2Cl2 (20 mL) and saturated NaHCO3 (20 mL). The layers were separated and the aqueous layer was further extracted with CH2Cl2 (2×20 mL). The combined CH2Cl2 layers were dried over Na2SO4, filtered, and concentrated in vacuo to provide the title compound. MS: m/z=329 (M+1).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe crude product was partitioned between CH2Cl2 (20 mL) and saturated NaHCO3 (20 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was further extracted with CH2Cl2 (2×20 mL)
  5. dry with materialThe combined CH2Cl2 layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fac15a02f567406face6b56c6d7f27e6
Source dataset
uspto-grants-2011_08
Patent number
US08003792B2

Reaction notes

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