(R)-(4-(1-(Benzyloxy)-3-fluoropropan-2-yl)-3-methylphenyl)boronic acid → (R)-(4-(1-Fluoro-3-hydroxypropan-2-yl)-3-methylphenyl)boronic acid

HRID 708886Notes

Reaction equation

HRID 708886 reaction equation
C([O:8][CH2:9][C@@H:10]([C:13]1[CH:18]=[CH:17][C:16]([B:19]([OH:21])[OH:20])=[CH:15][C:14]=1[CH3:22])[CH2:11][F:12])C1C=CC=CC=1>[Pd].CO>[F:12][CH2:11][C@H:10]([C:13]1[CH:18]=[CH:17][C:16]([B:19]([OH:21])[OH:20])=[CH:15][C:14]=1[CH3:22])[CH2:9][OH:8]

Participants

4

Reactant 1

HCID 123984577(R)-(4-(1-(Benzyloxy)-3-fluoropropan-2-yl)-3-methylphenyl)boronic acid

Product 1

HCID 123776672(R)-(4-(1-Fluoro-3-hydroxypropan-2-yl)-3-methylphenyl)boronic acidYield 71.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 24C (0.2 g, 0.662 mmol) was added Pd/C (0.070 g, 0.662 mmol) and MeOH (10 mL) under N2. The reaction was flush with N2 and degassed (3×). Then H2 balloon was introduced and system was degassed and flush with H2 (3×) before letting it stir at rt overnight. The mixture was filtered and washed with MeOH (3×). The filtrate was evaporated and dried under vacuo to give 24D (0.1 g, 0.472 mmol, 71.3% yield). 1H NMR (400 MHz, MeOD) δ ppm 7.36-7.46 (m, 2H) 7.23 (d, J=7.83 Hz, 1H) 4.68-4.78 (m, 1H) 4.56-4.67 (m, 1H) 3.66-3.93 (m, 2H) 3.37-3.53 (m, 1H) 2.31-2.46 (m, 3H); 19F NMR (376 MHz, MeOD) δ ppm −229.52-−222.26 (m, 1F).

Workup

  1. customThe reaction was flush with N2
  2. customdegassed (3×)
  3. additionThen H2 balloon was introduced
  4. customsystem was degassed
  5. customflush with H2 (3×)
  6. filtrationThe mixture was filtered
  7. washwashed with MeOH (3×)
  8. customThe filtrate was evaporated
  9. customdried under vacuo

Sources & evidence

ORD record
ord-fc02f98587ac498194c3d73f13e92ee1
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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