4,4-Dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-2-en-1-one → (S)-2-tert-butoxy-2-(1-(3,3-dimethyl-6-oxocyclohex-1-enyl)-3-methylnaphthalen-2-yl)acetic acid

HRID 514012Notes

Reaction equation

HRID 514012 reaction equation
[C:1]([O:5][C@@H:6]([C:10]1[C:19]([CH3:20])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1C1CCCCC=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH3:27][C:28]1([CH3:44])[CH2:33][CH2:32][C:31](=[O:34])[C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29]1>>[C:1]([O:5][C@@H:6]([C:10]1[C:19]([CH3:20])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[C:30]1[C:31](=[O:34])[CH2:32][CH2:33][C:28]([CH3:27])([CH3:44])[CH:29]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 102205804,4-Dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-2-en-1-oneHCID 56601711(S)-2-tert-butoxy-2-(1-cyclohexenyl-3-methylnaphthalen-2-yl)acetic acid

Product 1

HCID 67126043(S)-2-tert-butoxy-2-(1-(3,3-dimethyl-6-oxocyclohex-1-enyl)-3-methylnaphthalen-2-yl)acetic acid

Procedure

(S)-2-tert-Butoxy-2-(1-(3,3-dimethyl-6-oxocyclohex-1-enyl)-3-methylnaphthalen-2-yl)acetic acid (11) was prepared following the procedure to make (S)-2-tert-butoxy-2-(1-cyclohexenyl-3-methylnaphthalen-2-yl)acetic acid of Example 6 except that 4,4-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-2-enone was used instead of cyclohexenylboronic acid. Atropisomers were separated by flash column chromatography. 1H-NMR: 400 MHz, (CD3OD) δ: 7.72 (d, J=8.2 Hz, 1H), 7.59 (s,1H), 7.39 (m, 2H), 7.37 (m, 1H), 7.02 (s, 1H), 5.42 (s,1H), 2.82 (m, 1H), 2.67 (m, 1H), 2.58 (s, 3H), 2.18 (m, 2H), 1.38 (s, 6H), 1.08 (s, 9H). LCMS-ESI+ (m/z): [M−H]− calcd for C25H29O4: 393.50. found: 393.0.

Workup

  1. customAtropisomers were separated by flash column chromatography

Sources & evidence

ORD record
ord-ca434f2b5c8d4d0abe04c30ab5ceb43d
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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