Methanesulfonamide → (R)-1-(3-chlorophenyl)-2-hydroxybutan-1-one

HRID 1399553Notes

Reaction equation

HRID 1399553 reaction equation
C([Si]([O:8]/[C:9](/[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1)=[CH:10]\[CH2:11][CH3:12])(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:41]C)C=C4)N(CC2)C1.CS(N)(=O)=O>C(O)(C)(C)C.O>[Cl:19][C:15]1[CH:14]=[C:13]([C:9](=[O:8])[C@H:10]([OH:41])[CH2:11][CH3:12])[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 72879MethanesulfonamideHCID 112172021,4-Bis(dihydroquinidine)phthalazineHCID 46838070(Z)-tert-Butyl(1-(3-chlorophenyl)but-1-enyloxy)dimethylsilane

Product 1

HCID 46838211(R)-1-(3-chlorophenyl)-2-hydroxybutan-1-oneYield 85.2%

Reagents, catalysts & solvents 1

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

Procedure

Compound 10j was synthesized by a procedure similar to that described for (R)-10a using (Z)-tert-butyl(1-(3-chlorophenyl)but-1-enyloxy)dimethylsilane (9j, 3.7 g, 0.013 mol), AD-mix-β (17.5 g), and CH3SO2NH2 (1.2 g, 0.0126 mol) in tert-butyl alcohol-water (45 mL:45 mL). The reaction was quenched with sodium sulfite (12.5 g). After purification by column chromatography on silica gel, 2.2 g (79%) of the title product was isolated: [α]20D +31.4° (c 1.0, CHCl3); 1H NMR (CDCl3) δ 7.91-7.88 (m, 1H), 7.81-7.75 (m, 1H), 7.62-7.56 (m, 1H), 7.45 (t, 1H, J=7.8 Hz), 5.06-4.98 (m, 1H), 3.60 (d, 1H, J=6.5 Hz), 2.04-1.87 (m, 1H), 1.70-1.51 (m, 1H), 0.94 (t, 3H, J=7.4 Hz); 13C NMR (CDCl3) δ 201.4, 135.8, 135.7, 134.2, 130.6, 128.9, 126.9, 74.5, 29.1, 9.2. C10H11ClO2.

Workup

  1. customCompound 10j was synthesized by a procedure similar to
  2. customThe reaction was quenched with sodium sulfite (12.5 g)
  3. customAfter purification by column chromatography on silica gel

Sources & evidence

ORD record
ord-8940d613ffd64f45b4e7556724363c03
Source dataset
uspto-grants-2014_12
Patent number
US08906908B2

Reaction notes

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