Lithium Hydroxide → HCID 56601716, compound

HRID 514017Notes

Reaction equation

HRID 514017 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][C:24]([CH3:28])([CH3:27])[CH2:23][CH:22]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].CC1(C)C(C)(C)OB(C2CCC3(CC3)CC=2)O1.[OH-].[Li+]>>[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][C:24]2([CH2:28][CH2:27]2)[CH2:23][CH:22]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 231425414,4,5,5-Tetramethyl-2-(spiro[2.5]oct-5-en-6-yl)-1,3,2-dioxaborolaneHCID 56601715HCID 56601715, compound

Product 1

HCID 56601716HCID 56601716, compound

Conditions

Temperature
50 °C

Procedure

(S)-2-tert-butoxy-2-(3-methyl-1-(spiro[2.5]oct-5-en-6-yl)naphthalen-2-yl)acetic acid was prepared following the procedure for (S)-2-tert-butoxy-2-(1-(4,4-dimethylcyclohex-1-enyl)-3-methylnaphthalen-2-yl)acetic acid of Example 12 except using 4,4,5,5-tetramethyl-2-(spiro[2.5]oct-5-en-6-yl)-1,3,2-dioxaborolane instead of 2-(4,4-dimethylcyclohex-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and that in the final step the reaction was heated to 50° C. overnight followed by an addition of 10 equivalents of lithium hydroxide and heating to 60° C. for four hours and then at 45° C. overnight. 1H-NMR: 400 MHz, (CD3OD) δ: 7.90 (d, J=7.6 Hz, 1H), 7.71 (br d, J=7.2 Hz, 1H), 7.53 (d, J=8.0 Hz, 1H), 7.40 (m, 2H), 5.88 (s, 1H), 5.70 (s, 1H), 2.73 (m, 1H), 2.78 (s, 3H), 2.31 (m, 2H), 2.09 (m, 1H), 1.73 (m, 1H), 1.59 (m, 1H), 1.24 (s, 9H), 0.49 (m, 4H). LCMS-ESI− (m/z): [M−H]−calcd for C25H29O3: 377.22. found: 377.34.

Workup

  1. temperatureheating to 60° C. for four hours
  2. customat 45° C.
  3. customovernight

Sources & evidence

ORD record
ord-4342ffa778e04458bb50036fa388bd28
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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