HCID 67337039, compound → HCID 59708337, compound

HRID 1675790Notes

Reaction equation

HRID 1675790 reaction equation
C([Mg]Br)C.Br[C:6]1[CH:7]=[C:8]2[C:14]3([CH2:19][CH2:18][S:17][CH2:16][CH2:15]3)[C:13](=[O:20])[N:12]([CH2:21][C:22]([O-:24])=[O:23])[C:9]2=[CH:10][CH:11]=1.[Na+].C([Li])(C)(C)C>C1COCC1>[O:20]=[C:13]1[C:14]2([CH2:15][CH2:16][S:17][CH2:18][CH2:19]2)[C:8]2[C:9](=[CH:10][CH:11]=[CH:6][CH:7]=2)[N:12]1[CH2:21][C:22]([OH:24])=[O:23]

Participants

5

Reactant 3

HCID 67337039HCID 67337039, compound2×HCID 178418306HCID 178418306, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 59708337HCID 59708337, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethylmagnesium bromide (3 M in Et2O, 0.272 mL, 0.817 mmol) was added to a solution of sodium (5-bromo-2-oxo-2′,3′,5′,6′-tetrahydrospiro[indole-3,4′-thiopyran]-1(2H)-yl)acetate (194 mg, 0.545 mmol, described in Intermediate 20) in THF (5 mL) at −78° C., followed by the addition of tert-butyllithium (1.7 M in pentane, 0.801 mL, 1.36 mmol). After 1 h, the reaction was quenched with H2O and partitioned between EtOAc (20 mL) and 10% HCl (20 mL). The layers were separated and the aqueous layer was further extracted with EtOAc (2×10 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: m/z=278 (M+1).

Workup

  1. customthe reaction was quenched with H2O
  2. custompartitioned between EtOAc (20 mL) and 10% HCl (20 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was further extracted with EtOAc (2×10 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0853da3f28694390baa0281cba46f4be
Source dataset
uspto-grants-2011_08
Patent number
US08003792B2

Reaction notes

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