Methanesulfonamide → 1-Propanone, 2-hydroxy-1-phenyl-, (2R)-

HRID 1399546Notes

Reaction equation

HRID 1399546 reaction equation
C([Si]([O:8]/[C:9](/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][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:39]C)C=C4)N(CC2)C1.CS(N)(=O)=O>C(O)(C)(C)C.O>[C:12]1([C:9](=[O:8])[C@H:10]([OH:39])[CH3:11])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 72879MethanesulfonamideHCID 10377349HCID 10377349, compoundHCID 112172021,4-Bis(dihydroquinidine)phthalazine

Product 1

HCID 118049351-Propanone, 2-hydroxy-1-phenyl-, (2R)-Yield 80%

Reagents, catalysts & solvents 1

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

Procedure

Compound 10b was synthesized by a procedure similar to that described for (R)-10a using (Z)-tert-butyl(1-phenprop-1-enyloxy)dimethylsilane (9b, 7.2 g, 0.029 mol), AD-mix-β (40.7 g), and CH3SO2NH2 (2.8 g, 0.0294 mol) in tert-butyl alcohol-water (110 mL:110 mL) The reaction was quenched with sodium sulfite (29.1 g). After purification, 2.49 g (80%) of the title product was isolated: [α]20D +84.9° (c 1.6, CHCl3); 1H NMR (CDCl3) δ 7.96-7.90 (m, 2H), 7.66-7.58 (m, 1H), 7.54-7.47 (m, 2H), 5.23-5.12 (m, 1H), 3.84 (d, 1H, J=6.3 Hz), 1.45 (d, 3H, J=7.05 Hz); 13C NMR (CDCl3) δ 202.4, 134.0, 133.4, 128.9, 128.7, 69.3, 22.3. C9H10O2.

Workup

  1. customCompound 10b was synthesized by a procedure similar to
  2. customwas quenched with sodium sulfite (29.1 g)
  3. customAfter purification

Sources & evidence

ORD record
ord-3f29cbd822fd4d2d8f6e3b780afed32e
Source dataset
uspto-grants-2014_12
Patent number
US08906908B2

Reaction notes

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