(Cyclopent-1-en-1-yl)boronic acid → (S)-2-tert-butoxy-2-(1-cyclopentenyl-3-methylnaphthalen-2-yl)acetic acid

HRID 514013Notes

Reaction equation

HRID 514013 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]C[CH:22]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].C1(B(O)O)CCCC=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:21]1[CH2:26][CH2:25][CH2:24][CH:22]=1)[C:7]([OH:9])=[O:8])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 3861343(Cyclopent-1-en-1-yl)boronic acidHCID 56601711(S)-2-tert-butoxy-2-(1-cyclohexenyl-3-methylnaphthalen-2-yl)acetic acid

Product 1

HCID 56601713(S)-2-tert-butoxy-2-(1-cyclopentenyl-3-methylnaphthalen-2-yl)acetic acid

Procedure

(S)-2-tert-Butoxy-2-(1-cyclopentenyl-3-methylnaphthalen-2-yl)acetic acid (12) 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 cyclopentenylboronic acid was used instead of cyclohexenylboronic acid. 1H-NMR: 400 MHz, (CD3OD) δ: 7.78 (m, 1H), 7.53 (s,1H), 7.40 (m, 2H), 6.10-5.54 (m, 3H), 2.90 (m,1H), 2.65 (m, 5H), 2.57 (s, 3H), 1.18 (s, 9H). LCMS-ESI− (m/z): [M−H]-calcd for C22H25O3: 337.44. found: 337.1.

Sources & evidence

ORD record
ord-c406f0667a864c7588f674d5372b55ce
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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