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

HRID 1399547Notes

Reaction equation

HRID 1399547 reaction equation
C([Si]([O:8]/[C:9](/[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F: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>[F: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 46837928(Z)-tert-Butyl(1-(3-fluorophenyl)prop-1-enyloxy)dimethylsilane

Product 1

HCID 46838072(R)-1-(3-fluorophenyl)-2-hydroxypropan-1-oneYield 87.2%

Reagents, catalysts & solvents 1

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

Procedure

Compound 10c was synthesized by a procedure similar to that described for (R)-10a using (Z)-tert-butyl(1-(3-fluorophenyl)prop-1-enyloxy)dimethylsilane, (9c, 8.0 g, 0.030 mol), AD-mix-β (42.1 g), and CH3SO2NH2 (2.90 g, 0.0301 mol) in tert-butyl alcohol-water (120 mL:120 mL). The reaction was quenched with sodium sulfite (30.1 g). After purification, 4.4 g (87%) of the desired product 10c was isolated: [α]20D +58.1° (c 3.2, CHCl3); 1H NMR (CDCl3) δ 7.74-7.59 (m, 2H), 7.54-7.45 (m, 1H), 7.37-7.28 (m, 1H), 5.19-5.07 (m, 1H), 1.76 (d, 1H, J=6.3 Hz), 1.46 (d, 3H, J=6.9 Hz); 13C NMR (CDCl3) δ 201.6, 164.9, 131.0, (d), 124.7, 121.3 (d), 115.8 (d), 69.9, 22.4. C9H9FO2.

Workup

  1. customCompound 10c was synthesized by a procedure similar to
  2. customThe reaction was quenched with sodium sulfite (30.1 g)
  3. customAfter purification

Sources & evidence

ORD record
ord-f5bb6c92780d4532858b0eebd358879b
Source dataset
uspto-grants-2014_12
Patent number
US08906908B2

Reaction notes

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