Bis(pinacolato)diborane → HCID 178431083, compound

HRID 84232Notes

Reaction equation

HRID 84232 reaction equation
BrC1C=CC(OC[C@H]2CC[C@H](OC3CCCCO3)CC2)=CC=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.[CH3:41][C:42]1([CH3:70])[C:46]([CH3:48])([CH3:47])[O:45][B:44]([C:49]2[CH:69]=[CH:68][C:52]([O:53][CH2:54][C@@H:55]3[CH2:60][CH2:59][C@H:58]([O:61][CH:62]4[CH2:67][CH2:66][CH2:65][CH2:64][O:63]4)[CH2:57][CH2:56]3)=[CH:51][CH:50]=2)[O:43]1>>[CH3:47][C:46]1([CH3:48])[C:42]([CH3:41])([CH3:70])[O:43][B:44]([C:49]2[CH:50]=[CH:51][C:52]([O:53][CH2:54][C@H:55]3[CH2:56][CH2:57][C@H:58]([O:61][CH:62]4[CH2:67][CH2:66][CH2:65][CH2:64][O:63]4)[CH2:59][CH2:60]3)=[CH:68][CH:69]=2)[O:45]1

Participants

4

Reactant 3

HCID 2733548Bis(pinacolato)diboraneHCID 178419400HCID 178419400, compoundHCID 178431082HCID 178431082, compound

Product 1

HCID 178431083HCID 178431083, compound

Procedure

The title compound (624 mg, 61.5 mmol) was prepared from (+/−)-2-({trans-4-[(4-bromophenoxy)methyl]cyclohexyl}oxy)tetrahydro-2H-pyran (900 mg, 2.44 mmol) and bis(pinacolato)diborane (742 mg, 2.92 mmol) by a procedure analogous to that described for (+/−)-2-[(cis-4-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]methyl}cyclohexyl)oxy]tetrahydro-2H-pyran, Example 8, Step D. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.03-1.63 (m, 20 H) 1.65-1.90 (m, 3 H) 1.90-2.01 (m, 2 H) 2.03-2.15 (m, 2 H) 3.45-3.55 (m, 1 H) 3.55-3.67 (m, 1 H) 3.72-3.85 (m, 2 H) 3.89-3.97 (m, 1 H) 4.70-4.79 (m, 1 H) 6.88 (d, J=8.78 Hz, 2 H) 7.74 (d, J=8.78 Hz, 2 H)

Sources & evidence

ORD record
ord-30bf2f598fca47ccbb06812438ccca48
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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