3-Fluoro-4-methylbenzeneboronic acid → (R)-2-(2-Chloro-3'-fluoro-4'-methyl-biphenyl-4-ylmethyl)-morpholine-4-carboxylic Acid Tert-butyl Ester

HRID 2253040Notes

Reaction equation

HRID 2253040 reaction equation
C(N1CCO[C@H](CC2C=CC=C(C=CC3C=NC=CC=3)C=2)C1)(OC(C)(C)C)=O.[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][O:39][C@H:38]([CH2:42][C:43]2[CH:48]=[CH:47][C:46](OS(C(F)(F)F)(=O)=O)=[C:45]([Cl:57])[CH:44]=2)[CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30].[F:58][C:59]1[CH:60]=[C:61](B(O)O)[CH:62]=[CH:63][C:64]=1[CH3:65]>>[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][O:39][C@H:38]([CH2:42][C:43]2[CH:48]=[CH:47][C:46]([C:61]3[CH:62]=[CH:63][C:64]([CH3:65])=[C:59]([F:58])[CH:60]=3)=[C:45]([Cl:57])[CH:44]=2)[CH2:37]1)=[O:35])([CH3:31])([CH3:32])[CH3:30]

Participants

4

Reactant 3

HCID 27826743-Fluoro-4-methylbenzeneboronic acidHCID 67073511N-Boc-(R)-2-(3-(2-(3-pyridinyl)vinyl)-benzyl)morpholineHCID 86607061HCID 86607061, compound

Product 1

HCID 67073249(R)-2-(2-Chloro-3'-fluoro-4'-methyl-biphenyl-4-ylmethyl)-morpholine-4-carboxylic Acid Tert-butyl Ester

Procedure

The title compound was synthesized in analogy to example 80, intermediate (a), from (R)-2-(3-chloro-4-trifluoromethanesulfonyloxy-benzyl)-morpholine-4-carboxylic acid tert-butyl ester and 3-fluoro-4-methylbenzeneboronic acid to give the compound as a colorless oil (97%).

Sources & evidence

ORD record
ord-7ffd8ee697654385bdbbaa77dbddfb6c
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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