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

HRID 1399550Notes

Reaction equation

HRID 1399550 reaction equation
C([Si]([O:8]/[C:9](/[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[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:42]C)C=C4)N(CC2)C1.CS(N)(=O)=O>C(O)(C)(C)C.O>[N+:18]([C:14]1[CH:13]=[C:12]([C:9](=[O:8])[C@H:10]([OH:42])[CH3:11])[CH:17]=[CH:16][CH:15]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 72879MethanesulfonamideHCID 112172021,4-Bis(dihydroquinidine)phthalazineHCID 46838067(Z)-tert-Butyl-(1-(3-nitrophenyl)prop-1-enyloxy)dimethylsilane

Product 1

HCID 46838208(R)-1-(3-nitrophenyl)-2-hydroxypropan-1-oneYield 75.9%

Reagents, catalysts & solvents 1

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

Procedure

Compound 10g was synthesized by a procedure similar to that described for (R)-10a using (Z)-tert-butyl(1-(3-nitrophenyl)prop-1-enyloxy)dimethylsilane, (9g, 8.0 g, 0.027 mol), AD-mix-β (38 g), and CH3SO2NH2 (2.64 g, 0.0277 mol) in tert-butyl alcohol-water (110 mL:110 mL). The reaction was quenched with sodium sulfite (27.4 g). After purification by column chromatography on silica gel, 4.0 g (75%) of the desired product was isolated: [α]20D +63.8° (c 1.3, CHCl3); 1H NMR (CDCl3) δ 8.80-8.74 (m, 1H), 8.52-8.44 (m, 1H), 8.31-8.24 (m, 1H), 7.83-7.68 (m, 1H), 5.27-5.13 (m, 1H), 3.59 (d, 1H, J=6.5 Hz), 1.49 (d, 3H, J=7.08 Hz); 13C NMR (CDCl3) δ 200.4, 148.6, 134.9, 134.1, 130.2, 128.1, 121.6, 69.8, 21.9; C9H9NO4.

Workup

  1. customCompound 10g was synthesized by a procedure similar to
  2. customThe reaction was quenched with sodium sulfite (27.4 g)
  3. customAfter purification by column chromatography on silica gel

Sources & evidence

ORD record
ord-4d96b7becb894494905f9deb5bd1f880
Source dataset
uspto-grants-2014_12
Patent number
US08906908B2

Reaction notes

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