Methanesulfonamide → (R)-1-(3-Chlorophenyl)-2-hydroxypentan-1-one

HRID 1399554Notes

Reaction equation

HRID 1399554 reaction equation
C([Si]([O:8]/[C:9](/[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=1)=[CH:10]\[CH2:11][CH2:12][CH3:13])(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>[Cl:20][C:16]1[CH:15]=[C:14]([C:9](=[O:8])[C@H:10]([OH:42])[CH2:11][CH2:12][CH3:13])[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 72879MethanesulfonamideHCID 112172021,4-Bis(dihydroquinidine)phthalazineHCID 46838071(Z)-tert-Butyl(1-(3-chlorophenyl)pent-1-enyloxy)dimethylsilane

Product 1

HCID 46838212(R)-1-(3-Chlorophenyl)-2-hydroxypentan-1-oneYield 86.8%

Reagents, catalysts & solvents 1

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

Procedure

Compound 10k was synthesized by a procedure similar to that described for (R)-10a using (Z)-tert-butyl(1-(3-chlorophenyl)pent-1-enyloxy)dimethylsilane (9k, 4.1 g, 0.013 mol), AD-mix-β (18.5 g), and CH3SO2NH2 (1.3 g, 0.014 mol) in tert-butyl alcohol-water (50 mL:50 mL). The reaction was quenched with sodium sulfite (13.2 g). After purification, 2.4 g (77%) of the desired product was isolated: [α]20D +33.3° (c 1.1, CHCl3); 1H NMR (CDCl3) δ 7.91-7.87 (m, 1H), 7.80-7.75 (m, 1H), 7.63-7.17 (m, 1H), 7.45 (t, 1H, J=7.6 Hz), 5.08-5.00 (m, 1H), 3.58 (d, 1H, J=6.5 Hz), 1.89-1.75 (m, 1H), 1.61-1.35 (m, 3H), 0.93 (t, 3H, J=7.2 Hz); 13C NMR (CDCl3) δ 201.1, 135.4, 133.8, 130.2, 128.6, 126.5, 73.2, 37.8, 18.2, 13.8. C11H13ClO2.

Workup

  1. customCompound 10k was synthesized by a procedure similar to
  2. customThe reaction was quenched with sodium sulfite (13.2 g)
  3. customAfter purification

Sources & evidence

ORD record
ord-35fde3b6209944bcac0581b8b6869536
Source dataset
uspto-grants-2014_12
Patent number
US08906908B2

Reaction notes

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