O-(Tetrahydropyran-2-yl)hydroxylamine → (2R)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanamide

HRID 533508Notes

Reaction equation

HRID 533508 reaction equation
[CH3:1][C@@:2]([S:23]([CH3:26])(=[O:25])=[O:24])([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([B:14]2[O:18][C:17]([CH3:20])([CH3:19])[C:16]([CH3:22])([CH3:21])[O:15]2)=[CH:10][CH:9]=1)[C:3]([OH:5])=O.[O:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]1[O:33][NH2:34].BrC1C=CC(CCC(C)(S(C)(=O)=O)C(NOC2CCCCO2)=O)=CC=1>>[CH3:1][C@@:2]([S:23]([CH3:26])(=[O:24])=[O:25])([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([B:14]2[O:15][C:16]([CH3:21])([CH3:22])[C:17]([CH3:20])([CH3:19])[O:18]2)=[CH:10][CH:9]=1)[C:3]([NH:34][O:33][CH:28]1[CH2:29][CH2:30][CH2:31][CH2:32][O:27]1)=[O:5]

Participants

4

Reactant 3

HCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 66578010(2R)-2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanoic acidHCID 76445393(+/-)-4-(4-Bromophenyl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 56950325(2R)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanamideYield 77.5%

Procedure

The title compound (7.2 g, 77%) was prepared from (2R)-2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanoic acid (7.4 g, 19.3 mmol) and O-tetrahydro-2H-pyran-2-yl-hydroxylamine (3.3 g, 28 mmol) by a procedure analogous to that described for (+/−)-4-(4-bromophenyl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide as in Preparation 3 step C. LCMS m/z 480.8 (M−1).

Sources & evidence

ORD record
ord-682dda02bc6744e3bb596667b481f978
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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