3-(Tert-butyldimethylsilyl)oxy-1-(methylsulfonyloxy)cyclohexane → 2-[3-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole

HRID 389450Notes

Reaction equation

HRID 389450 reaction equation
[C:1]([Si:5]([CH3:19])([CH3:18])[O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH:9](OS(C)(=O)=O)[CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[Si](OC1CCC([N:33]2[CH2:37][C:36]([B:38]3[O:42][C:41]([CH3:44])([CH3:43])[C:40]([CH3:46])([CH3:45])[O:39]3)=[CH:35][NH:34]2)C1)(C(C)(C)C)(C)C>>[C:1]([Si:5]([CH3:19])([CH3:18])[O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH:9]([N:33]2[CH2:37][C:36]([B:38]3[O:39][C:40]([CH3:46])([CH3:45])[C:41]([CH3:44])([CH3:43])[O:42]3)=[CH:35][NH:34]2)[CH2:8]1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 226292523-(Tert-butyldimethylsilyl)oxy-1-(methylsulfonyloxy)cyclohexaneHCID 667595192-[3-(tert-butyldimethylsilanyloxy)-cyclopentyl]-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 667600172-[3-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazoleYield 10%

Procedure

The title compound was prepared in 10% yield from methanesulfonic acid 3-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl ester by a procedure analogous to Intermediate 28, Step C. The crude compound was purified by column chromatography (25% ethyl acetate:hexanes and then DCM) to afford the title compound. 1H NMR (300 MHz, CDCl3): δ 7.76 (s, 1H), 7.27 (s, 1H), 4.45-4.63 (m, 1H), 4.23 (br. s, 1H), 2.05-2.09 (m, 2H), 1.5-1.9 (m, 6H), 1.45 (s, 9H), 1.31 (s, 12H), 0.05 (s, 6H).

Workup

  1. customThe crude compound was purified by column chromatography (25% ethyl acetate
  2. customhexanes and then DCM) to afford the title compound

Sources & evidence

ORD record
ord-0b790e85d8254374bf8129c5265c1258
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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