Methyl Acetate → HCID 67384718, compound

HRID 2096618Notes

Reaction equation

HRID 2096618 reaction equation
[C:1]([O:4][CH3:5])(=[O:3])[CH3:2].[Li+].CC([N-]C(C)C)C.[Br:14][C:15]1[CH:16]=[C:17]2[C:27](=[CH:28][CH:29]=1)[O:26][C:20]1([CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH2:19]/[C:18]/2=[N:30]\[S:31]([C:34]([CH3:37])([CH3:36])[CH3:35])(=O)=[O:32]>C1COCC1>[Br:14][C:15]1[CH:16]=[C:17]2[C:27](=[CH:28][CH:29]=1)[O:26][C:20]1([CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH2:19][C:18]2([CH2:2][C:1]([O:4][CH3:5])=[O:3])[NH:30][S:31]([C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32]

Participants

5

Reactant 3

HCID 6584Methyl AcetateHCID 2724682Lithium diisopropylamideHCID 87380325HCID 87380325, compound

Product 1

HCID 67384718HCID 67384718, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of methyl acetate (1.86 g, 0.025 mol) in THF (18 mL) was added LDA (2 M in THF) was added dropwise via a syring at −78° C. After stirring at −78° C. for 30 minutes, a solution of (E)-N-(6-bromospiro[chroman-2,1′-cyclohexane]-4-ylidene)-2-methylpropane-2-sulfonamide (5.0 g, 0.0126 mol) in THF (7.4 mL) was added dropwise via a syring. The mixture was stirring at −78° C. for 3 h. The reaction was quenched with aqueous NH4Cl solution and allowed to warming to room temperature. The mixture was diluted with water and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated to give the product, which was purified by chromatography to afford methyl 2-(6-bromo-4-(1,1-dimethylethylsulfinamido)spiro[chroman-2,1′-cyclohexane]-4-yl)acetate (1.4 g, 33%). 1H NMR (CDCl3): 1.23 (s, 9H), 1.36-1.52 (m, 4H), 1.57 (m, 1H), 1.66 (m, 3H), 1.86 (d, 2H), 2.24 (d, 1H), 2.67 (d, 1H), 2.93 (s, 3H), 3.71 (s, 3H), 5.34 (s, 1H), 6.79 (d, 1H), 7.26 (s, 1H), 7.39 (s, 1H).

Workup

  1. additionwas added dropwise via a syring at −78° C
  2. stirringThe mixture was stirring at −78° C. for 3 h
  3. customThe reaction was quenched with aqueous NH4Cl solution
  4. temperatureto warming to room temperature
  5. additionThe mixture was diluted with water
  6. extractionextracted with EtOAc
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give the product, which
  11. customwas purified by chromatography

Sources & evidence

ORD record
ord-d6eb463d296f43749c5a272e8ef1a19a
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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