Bis(pinacolato)diborane → ethyl (2R)-2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanoate

HRID 533506Notes

Reaction equation

HRID 533506 reaction equation
BrC1C=CC(CC[C@@](C)(S(C)(=O)=O)C(OCC)=O)=CC=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.[CH3:39][C:40]([S:63]([CH3:66])(=[O:65])=[O:64])([CH2:46][CH2:47][C:48]1[CH:53]=[CH:52][C:51]([B:54]2[O:58][C:57]([CH3:60])([CH3:59])[C:56]([CH3:62])([CH3:61])[O:55]2)=[CH:50][CH:49]=1)[C:41]([O:43][CH2:44][CH3:45])=[O:42]>>[CH3:39][C@@:40]([S:63]([CH3:66])(=[O:64])=[O:65])([CH2:46][CH2:47][C:48]1[CH:49]=[CH:50][C:51]([B:54]2[O:58][C:57]([CH3:59])([CH3:60])[C:56]([CH3:62])([CH3:61])[O:55]2)=[CH:52][CH:53]=1)[C:41]([O:43][CH2:44][CH3:45])=[O:42]

Participants

4

Reactant 3

HCID 2733548Bis(pinacolato)diboraneHCID 66578009ethyl (2R)-4-(4-bromophenyl)-2-methyl-2-(methylsulfonyl)butanoateHCID 66578081Ethyl 2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanoate

Product 1

HCID 66577950ethyl (2R)-2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanoateYield 93%

Procedure

The title compound (10.5 g, 93%) was prepared from ethyl(2R)-4-(4-bromophenyl)-2-methyl-2-(methylsulfonyl)butanoate, (10.0 g, 27.5 mmol) and bis(pinacolato)diborane (7.69 g, 30.3 mmol) by a procedure analogous to that described for (+/−)-ethyl 2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanoate as described in Preparation 3 step A.

Workup

  1. customas described in Preparation 3 step A

Sources & evidence

ORD record
ord-87ca4d7be3a446d5be1cf3c621a1f02b
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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