Acetic Acid → [(S)-6-((R)-7-Fluoro-4-hydroxyindan-1-yloxy)-2,3-dihydrobenzofuran-3-yl]-acetic acid methyl ester

HRID 2170935Notes

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](B5OC(C)(C)C(C)(C)O5)[CH:20]=[CH:21][C:22]=4[F:24])[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1.C(O)(=[O:37])C.O.B(O[O-])=O.[Na+]>CCO.C1(C)C=CC=CC=1>[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]([OH:37])[CH:20]=[CH:21][C:22]=4[F:24])[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

4.41 g (8.72 mmol) {(S)-6-[(R)-7-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indan-1-yloxy]-2,3-dihydrobenzofuran-3-yl}-acetic acid methyl ester is dissolved in 10 ml EtOH and 2.20 ml glacial acetic acid and 2.20 ml water are added. The funnel is rinsed with 7.50 ml EtOH. Then, 2.28 g (14.8 mmol) sodium perborate is added in portions at r.t. and the mixture is stirred. After complete addition, 1.40 ml water and 1.6 ml toluene is added. The organic phase is separated and 1.60 ml water is added. After cooling to 0° C., the 2-phasic mixture is seeded and stirring is continued. The precipitated product is filtered off, washed with cold toluene and dried. Yield: 2.86 g; Rf=0.22 (silica gel, PE/EtOAc=7/3); Mass spectrum (ESI): m/z=359 [M+H]+.

Workup

washThe funnel is rinsed with 7.50 ml EtOH
additionis added
customThe organic phase is separated
addition1.60 ml water is added
stirringstirring
filtrationThe precipitated product is filtered off
washwashed with cold toluene
customdried

Sources & evidence

ORD record: ord-2c6185e6a9e6463c8f7c706a83b66aa3
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051289B2

Reaction notes

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