4,4,6-Trimethyl-2-vinyl-1,3,2-dioxaborinane → (3R)-3-fluoro-1-(4-((E)-2-(4,4,6-trimethyl-1,3,2-dioxaborinan-2-yl)vinyl)benzyl)pyrrolidine

HRID 447552

Reaction equation

HRID 447552 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][C@@H:9]([F:12])[CH2:8]2)=[CH:4][CH:3]=1.[CH3:15][C:16]1([CH3:25])[CH2:21][CH:20]([CH3:22])[O:19][B:18]([CH:23]=[CH2:24])[O:17]1>>[F:12][C@@H:9]1[CH2:10][CH2:11][N:7]([CH2:6][C:5]2[CH:13]=[CH:14][C:2](/[CH:24]=[CH:23]/[B:18]3[O:17][C:16]([CH3:25])([CH3:15])[CH2:21][CH:20]([CH3:22])[O:19]3)=[CH:3][CH:4]=2)[CH2:8]1

Participants

3

Reactant 2

HCID 1073104,4,6-Trimethyl-2-vinyl-1,3,2-dioxaborinaneHCID 66730391(R)-1-(4-bromobenzyl)-3-fluoropyrrolidine

Product 1

HCID 66734517(3R)-3-fluoro-1-(4-((E)-2-(4,4,6-trimethyl-1,3,2-dioxaborinan-2-yl)vinyl)benzyl)pyrrolidine

Procedure

The title compound was synthesized according to the method of Example A51A, except substituting (R)-1-(4-bromobenzyl)-3-fluoropyrrolidine (1.07 g, 4.15 mmol) and 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane (0.77 mL, 4.57 mmol) which gave 1.40 g, 91% of a pale orange solid; MS ESI [M+H]+ 332.3, calcd for [C19H27BFNO2+H]+ 332.22.

Sources & evidence

ORD record
ord-e2be3fe498234a09b96b5324f7708bb7
Source dataset
uspto-grants-2013_07
Patent number
US08481525B2

Linked notes

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