{(S)-6-[(R)-7-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester → (R)-7-Fluoro-1-[(S)-3-methoxycarbonylmethyl-2,3-dihydrobenzofuran-6-yloxy]-2,3-dihydro-1H-inden-4-ylboronic acid

HRID 2408568Notes

Reaction equation

HRID 2408568 reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@H:15]3[C:23]4[C:18](=[C:19]([B:25]5[O:29]C(C)(C)C(C)(C)[O:26]5)[CH:20]=[CH:21][C:22]=4[F:24])[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1>CC(C)=O.O>[F:24][C:22]1[CH:21]=[CH:20][C:19]([B:25]([OH:29])[OH:26])=[C:18]2[C:23]=1[C@H:15]([O:14][C:12]1[CH:11]=[CH:10][C:9]3[C@H:5]([CH2:4][C:3]([O:2][CH3:1])=[O:34])[CH2:6][O:7][C:8]=3[CH:13]=1)[CH2:16][CH2:17]2

Participants

4

Reactant 1

HCID 86697106{(S)-6-[(R)-7-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

Product 1

HCID 86720141(R)-7-Fluoro-1-[(S)-3-methoxycarbonylmethyl-2,3-dihydrobenzofuran-6-yloxy]-2,3-dihydro-1H-inden-4-ylboronic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

{(S)-6-[(R)-7-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester (3.00 g) is dissolved in acetone (20 mL) and water (10 mL). NaIO4 (5.90 g) and NH4O2CCH3 (2.85 g) are added. The mixture is stirred at room temperature for 36 h. Water is added and the resulting mixture is extracted with ethyl acetate. The combined extract is dried (Na2SO4) and concentrated to give the title compound LC (method 12): tR=1.02 min; Mass spectrum (ESI+): m/z=387 [M+H]+.

Workup

  1. extractionthe resulting mixture is extracted with ethyl acetate
  2. extractionThe combined extract
  3. dry with materialis dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-216dbadec78f42468304a975c315215b
Source dataset
uspto-grants-2014_08
Patent number
US08815864B2

Reaction notes

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