Methanesulfonamide → (R)-1-(3-bromophenyl)-2-hydroxypropan-1-one

HRID 1399548Notes

Reaction equation

HRID 1399548 reaction equation
C([Si]([O:8]/[C:9](/[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Br: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>[Br: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 112172021,4-Bis(dihydroquinidine)phthalazineHCID 46838064(Z)-tert-Butyl(1-(3-bromophenyl)prop-1-enyloxy)dimethylsilane

Product 1

HCID 46838073(R)-1-(3-bromophenyl)-2-hydroxypropan-1-oneYield 88%

Reagents, catalysts & solvents 1

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

Procedure

Compound 10d was synthesized by a procedure similar to that described for (R)-10a using (Z)-tert-butyl(1-(3-bromophenyl)prop-1-enyloxy)dimethylsilane, (9d, 1.15 g, 0.0035 mol), AD-mix-β (4.9 g), and CH3SO2NH2 (334 mg, 3.5 mmol) in tert-butyl alcohol-water (17.5 mL. 17.5 mL). The reaction was quenched with sodium sulfite (3.5 g). After purification by column chromatography on silica gel, 0.700 g (88%) of the desired product was isolated: [α]20D +61.1° (c 1.3, CHCl3); 1H NMR (CDCl3) δ 8.09-8.04 (m, 1H), 7.87-7.81 (m, 1H), 7.78-7.72 (m, 1H), 7.39 (t, 1H, J=8.0 Hz), 5.18-5.05 (m, 1H), 3.66 (d, 1H, J=6.4 Hz), 1.45 (d, 3H, J=7.2 Hz); 13C NMR (CDCl3) δ 201.2, 136.8, 135.2, 131.6, 130.4, 127.1, 123.3, 69.5, 22.1. C9H9BrO2.

Workup

  1. customCompound 10d was synthesized by a procedure similar to
  2. customThe reaction was quenched with sodium sulfite (3.5 g)
  3. customAfter purification by column chromatography on silica gel

Sources & evidence

ORD record
ord-905224c706974e12bda9971c131b308e
Source dataset
uspto-grants-2014_12
Patent number
US08906908B2

Reaction notes

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