2-Amino-2-phenylethan-1-ol → (S)-(+)-3,4-dihydroxy-5-methyl-5-[4-(2-methylpropyl)phenyl]-2(5H)-furanone

HRID 612571Notes

Reaction equation

HRID 612571 reaction equation
C(C1C=CC([C:9]([C:11]([O:13]CC)=[O:12])=[O:10])=CC=1)C(C)C.C1C=CC([C@H](N)CO)=CC=1.[CH2:28]([C:32]1[CH:37]=[CH:36][C:35]([C@H:38]([CH3:43])[C:39]([O:41]C)=O)=[CH:34][CH:33]=1)[CH:29]([CH3:31])[CH3:30]>>[OH:10][C:9]1[C:11](=[O:12])[O:13][C@@:38]([CH3:43])([C:35]2[CH:34]=[CH:33][C:32]([CH2:28][CH:29]([CH3:30])[CH3:31])=[CH:37][CH:36]=2)[C:39]=1[OH:41]

Participants

4

Reactant 3

HCID 1347972-Amino-2-phenylethan-1-olHCID 6933487Methyl (alphaS)-alpha-methyl-4-(2-methylpropyl)benzeneacetateHCID 12585534Ethyl 4-iso-butylbenzoylformate

Product 1

HCID 70247960(S)-(+)-3,4-dihydroxy-5-methyl-5-[4-(2-methylpropyl)phenyl]-2(5H)-furanoneYield 19%

Procedure

(S)-(+)-3,4-Dihydroxy-5-methyl-5-[4-(2-methylpropyl)phenyl]-2(5H)-furanone was synthesized in an analogous manner used for the production of(R)-(-)-5-[(1,1'-biphenyl)-4-yl]-3,4-dihydroxy-5-methyl-2(5H)-furanone starting with ethyl 4-isobutylbenzoylformate. (S)-(+)-Phenylglycinol was used to resolve the methyl (S)-(+)-2-(4-isobutylphenyl)propionate enantiomer, of which 1.2 g (5 mmol) was converted into 250 mg (19% yield) of (S)-(+)-3,4-dihydroxy-5-methyl-5-[4-(2-methylpropyl)phenyl]-2(5H)-furanone as a white crystalline material: mp 175-177° C. dec. (CHCl3 /hexanes); [α]25D +132° (c=1.55; MeOH) 1H NMR (acetone-d6) δ 7.44-7.14 (m, 4H), 2.48 (d, 2H, J=7.1 Hz), 1.87-1.82 (m, 1H), 1.83 (s, 3H), 0.88 (d, 6H, J=6.5 Hz). Anal Calcd for C15H18O4 : C, 68.68; H, 6.92. Found: C, 68.08; H, 6.90.

Workup

  1. custom(S)-(+)-3,4-Dihydroxy-5-methyl-5-[4-(2-methylpropyl)phenyl]-2(5H)-furanone was synthesized in an analogous manner

Sources & evidence

ORD record
ord-9ded5f90fb4d4cc58fc081043067ec02
Source dataset
uspto-grants-1999_12
Patent number
US06005000

Reaction notes

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