tert-butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-yl)oxy)silane → tert-butyl-dimethyl-[(1R)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indan-1-yl]oxy-silane

HRID 1891451Notes

Reaction equation

HRID 1891451 reaction equation
BrC1C=CC=C2C=1CC[C@H]2O[Si](C(C)(C)C)(C)C.[C:19]([Si:23]([CH3:44])([CH3:43])[O:24][CH:25]1[C:33]2[C:28](=[C:29]([B:34]3[O:38][C:37]([CH3:40])([CH3:39])[C:36]([CH3:42])([CH3:41])[O:35]3)[CH:30]=[CH:31][CH:32]=2)[CH2:27][CH2:26]1)([CH3:22])([CH3:21])[CH3:20]>>[C:19]([Si:23]([CH3:44])([CH3:43])[O:24][C@H:25]1[C:33]2[C:28](=[C:29]([B:34]3[O:35][C:36]([CH3:42])([CH3:41])[C:37]([CH3:40])([CH3:39])[O:38]3)[CH:30]=[CH:31][CH:32]=2)[CH2:27][CH2:26]1)([CH3:22])([CH3:21])[CH3:20]

Participants

3

Reactant 2

HCID 58354997tert-butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-yl)oxy)silaneHCID 67198512(R)-((4-bromo-2,3-dihydro-1H-inden-1-yl)oxy)(tert-butyl)dimethylsilane

Product 1

HCID 67302554tert-butyl-dimethyl-[(1R)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indan-1-yl]oxy-silane

Procedure

(R)-tert-butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-yl)oxy)silane IND INT-7 was prepared in an analogous fashion using (R)-((4-bromo-2,3-dihydro-1H-inden-1-yl)oxy)(tert-butyl)dimethylsilane IND INT-4. Racemic (±)-tert-butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-yl)oxy)silane IND INT-8 was prepared in an analogous fashion from IND INT-5.

Workup

  1. customwas prepared in an analogous fashion from IND INT-5

Sources & evidence

ORD record
ord-31c2cac7c3d141f1b081e3fa30a27095
Source dataset
uspto-grants-2013_08
Patent number
US08507538B2

Reaction notes

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