2-Methyl-3-butyn-2-ol → (S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-7-(3-hydroxy-3-methylbut-1-ynyl)-3-methylnaphthalen-2-yl)acetic acid

HRID 514099Notes

Reaction equation

HRID 514099 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14](OS(C(F)(F)F)(=O)=O)=[CH:15][CH:16]=3)[CH:11]=[C:10]([CH3:26])[C:9]=2[C@H:27]([OH:33])[C:28]([O:30]CC)=[O:29])=[CH:4][CH:3]=1.[BH4-].[Na+].BrC1C=[C:45]2[C:40]([CH:41]=C(C)C(C(=O)C(OCC)=O)=C2C2C=CC(Cl)=CC=2)=[CH:39]C=1.[CH3:62][C:63]([OH:67])([C:65]#[CH:66])[CH3:64]>CC#N.O>[C:40]([O:33][C@@H:27]([C:9]1[C:10]([CH3:26])=[CH:11][C:12]2[C:17](=[CH:16][C:15]([C:66]#[C:65][C:63]([OH:67])([CH3:64])[CH3:62])=[CH:14][CH:13]=2)[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:28]([OH:30])=[O:29])([CH3:45])([CH3:41])[CH3:39]

Participants

6

Reactant 4

HCID 82582-Methyl-3-butyn-2-olHCID 4311764Sodium borohydrideHCID 67126218Ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-oxoacetateHCID 86691546(S)-ethyl 2-(1-(4-chlorophenyl)-3-methyl-6-(trifluoromethylsulfonyloxy) naphthalen-2-yl)-2-hydroxyacetate

Product 1

HCID 67126977(S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-7-(3-hydroxy-3-methylbut-1-ynyl)-3-methylnaphthalen-2-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

(S)-2-tert-Butoxy-2-(1-(4-chlorophenyl)-7-(3-hydroxy-3-methylbut-1-ynyl)-3-methylnaphthalen-2-yl)acetic acid (99) was prepared by the method of Example 67 using the reduction method of Example 51 step 3 for (S)-ethyl 2-(1-(4-chlorophenyl)-3-methyl-6-(trifluoromethylsulfonyloxy) naphthalen-2-yl)-2-hydroxyacetate instead of step 5, NaBH4 step, from ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-oxoacetate. The remainder of the sequence follows the method of Example 67 using 2-methylbut-3-yn-2-ol in Step 7. 1H-NMR: 400 MHz, (CD3OD) δ: 7.73 (d, J=9 Hz, 1H), 7.67 (s, 1H), 7.57 (m, 3H), 7.38 (d, J=9 Hz, 1H), 7.30 (d, J=9 Hz, 1H), 7.26 (s, 1H), 5.16 (s, 1H), 2.60 (s, 3H), 1.51 (s, 6H), 0.98 (s, 9H). HPLC (Kinetex 2.6u, 50×4.6 mm, 2-100% MeCN/H2O+0.05% HOAc, 5 min run): tR (min)=3.40.

Sources & evidence

ORD record
ord-948226ac4846451f9cb190fcf5a55176
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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