Methanesulfonamide → (S)-1-(3-Chlorophenyl)-2-hydroxy-1-propanone

HRID 1399545Notes

Reaction equation

HRID 1399545 reaction equation
C([Si]([O:8]/[C:9](/[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)=[CH:10]\[CH3:11])(C)C)(C)(C)C.CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:40]C)C=C4)N(CC2)C1.CS(N)(=O)=O>C(O)(C)(C)C.O>[Cl:18][C:14]1[CH:13]=[C:12]([C:9](=[O:8])[C@@H:10]([OH:40])[CH3:11])[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 72879MethanesulfonamideHCID 113005611-Chloro-3-[(1Z)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-propen-1-yl]-benzeneHCID 510036741-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine

Product 1

HCID 10313420(S)-1-(3-Chlorophenyl)-2-hydroxy-1-propanone

Reagents, catalysts & solvents 1

HCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

Compound (S)-10a was synthesized by a procedure similar to that described for (R)-10a using (Z)-tert-butyl(1-(3-chlorophenyl)prop-1-enyloxy)dimethylsilane (9a, 8.8 g, 0.031 mol), AD-mix-α (43.5 g), and CH3SO2NH2 (3a, 3 g, 0.032 mol) in tert-butyl alcohol-water (120 mL:120 mL). The reaction mixture was quenched with sodium sulfite (31.1 g). After purification, 4.51 g (78%) of the (S)-10a was isolated. Characterization data is similar with data reported in Fang, Q. K.; Han, Z.; Grover, P.; Kessler, D.; Senanayake, C. H.; Wald, S. A., Tetrahedron: Asymmetry 2000, 11, 3659-3663.

Workup

  1. customCompound (S)-10a was synthesized by a procedure similar to
  2. customThe reaction mixture was quenched with sodium sulfite (31.1 g)
  3. customAfter purification, 4.51 g (78%) of the (S)-10a
  4. customwas isolated

Sources & evidence

ORD record
ord-4b2d58a84d4b4a7cb683b16cf81e4086
Source dataset
uspto-grants-2014_12
Patent number
US08906908B2

Reaction notes

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