4-Methylcyclohexen-1-ylboronic acid → (2S)-2-tert-Butoxy-2-(3-methyl-1-(4-methylcyclohex-1-enyl)naphthalen-2-yl)acetic acid

HRID 514014Notes

Reaction equation

HRID 514014 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]=1[C:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH3:27]C1CCC(B(O)O)=CC1>>[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:21]1[CH2:26][CH2:25][CH:24]([CH3:27])[CH2:23][CH:22]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 441195564-Methylcyclohexen-1-ylboronic acidHCID 56601711(S)-2-tert-butoxy-2-(1-cyclohexenyl-3-methylnaphthalen-2-yl)acetic acid

Product 1

HCID 56601714(2S)-2-tert-Butoxy-2-(3-methyl-1-(4-methylcyclohex-1-enyl)naphthalen-2-yl)acetic acid

Procedure

(2S)-2-tert-Butoxy-2-(3-methyl-1-(4-methylcyclohex-1-enyl)naphthalen-2-yl)acetic acid 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-methylcyclohex-1-enylboronic acid was used instead of cyclohexenylboronic acid. 1H-NMR: 400 MHz, (CD3OD) δ: 7.92-7.78 (m, 1H), 7.70 (m,1H), 7.52 (s, 1H), 7.39 (m, 2H), 6.10-5.58 (m, 2H), 2.56 (s,3H), 2.65-1.84 (m, 6H), 1.50 (m, 1H), 1.22 (s, 9H), 1.14 (t, 3H). LCMS-ESF (m/z): [M−H]− calcd for C24H29O3: 365.49. found: 365.1.

Sources & evidence

ORD record
ord-13801b14dec84368aa7dc5bdb2b32cc2
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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