(2S)-7-(Benzyloxy)-1-(4-fluorophenoxy)heptan-2-OL → (6S)-7-(4-fluorophenoxy)-heptane-1,6-diol

HRID 413576Notes

Reaction equation

HRID 413576 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C@H:14]([OH:24])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)C1C=CC=CC=1>C(O)C.[Pd]>[F:23][C:20]1[CH:19]=[CH:18][C:17]([O:16][CH2:15][C@@H:14]([OH:24])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:8])=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 59904757(2S)-7-(Benzyloxy)-1-(4-fluorophenoxy)heptan-2-OL

Product 1

HCID 59971312(6S)-7-(4-fluorophenoxy)-heptane-1,6-diolYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (2S)-7-Benzyloxy-1-(4-fluorophenoxy)-heptane-2-ol (5.8 g, 17.5 mmol) in ethanol (30 ml), 10% of Pd/C (100 mg) was added and stirred under H2 atmosphere at normal temperature and pressure for 3 hours. The reaction mixture was filtered through celite, washed with ethanol and concentrated. The residue was purified by silicia gel chromatography using EtOAc-hexane (1:1) to give (6S)-7-(4-fluorophenoxy)-heptane-1,6-diol (3.92 g, 93%); [α]D+12 (c 3.1, CHCl3), 1H-NMR (CDCl3, 200 Hz): δ 1.29-1.69 (m, 8H), 3.65 (t, J=6.8 Hz, 2H), 3.82-4.02 (m, 2H), 6.75-7.0 (m, 4H); HRMS (EI): calcd. for C13H19O3F(M+) 242.131823 found 242.131900.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with ethanol
  3. concentrationconcentrated
  4. customThe residue was purified by silicia gel chromatography

Sources & evidence

ORD record
ord-a24bbfc303084d348663f8d9a6cafda1
Source dataset
uspto-grants-2003_05
Patent number
US06566538B1

Reaction notes

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