HCID 67550769, compound → HCID 67550767, compound

HRID 433150Notes

Reaction equation

HRID 433150 reaction equation
C([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[CH2:19][CH2:20][C@H:21]([OH:24])[CH2:22][OH:23])C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[CH2:19][CH2:20][C@H:21]([OH:24])[CH2:22][OH:23]

Participants

4

Reactant 1

HCID 67550769HCID 67550769, compound

Product 1

HCID 67550767HCID 67550767, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (2S)-4-[1-(benzyloxy)-2-naphthyl]-1,2-butanediol (5.63 g, 17.5 mmol) in ethanol (150 mL), palladium on carbon (10 wt. %, 0.56 g) was added, and the reaction mixture was shaken under an H2 atmosphere (50 psi) for 6 h. The reaction mixture was filtered (celite) and the solvent removed in vacuo to provide a crude oil. Purification by flash column chromatography (silica, ethyl acetate:hexanes 4:1) gave 3.81 g (94%, 50% ee) of (2S)-4-(1-hydroxy-2-naphthyl)-1,2-butanediol as a colorless oil which crystallizes upon standing. [α]D25=+11.93 (c 10.06 in chloroform, 50% ee); Rf=0.50 (silica, ethyl acetate:hexanes 4:1); mp 105-108° C.; Anal. Calcd. for C14H16O3: C, 72.39; H, 6.94. Found: C, 72.20; H, 7.18.

Workup

  1. filtrationThe reaction mixture was filtered (celite)
  2. customthe solvent removed in vacuo
  3. customto provide a crude oil
  4. customPurification by flash column chromatography (silica, ethyl acetate:hexanes 4:1)

Sources & evidence

ORD record
ord-4873a93697214485b0ae7835490d2771
Source dataset
uspto-grants-2003_12
Patent number
US06667322B2

Reaction notes

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