Sodium borohydride → 2-Tert-butoxy-2-(1-(4-chlorophenyl)-3,6-dimethylnaphthalen-2-yl)acetic acid
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]=[C:15]([C:21]3C=CN=CC=3)[CH:16]=2)[C:11]=1[C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].CC1CC2C(=CC=C(C)C=2)C(=O)C1.[BH4-].[Na+]>CCO>[C:1]([O:5][CH:6]([C:10]1[C:19]([CH3:20])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH3:21])[CH:16]=2)[C:11]=1[C:27]1[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2-tert-Butoxy-2-(1-(4-chlorophenyl)-3,6-dimethylnaphthalen-2-yl)acetic acid (58) was prepared with a route similar to that described for compound 53 of Example 51 beginning with 3,6-dimethyl-3,4-dihydronaphthalen-1(2H)-one (prepared from 1-(3-methylphenyl)propan-2-one) and omitting steps 5 and 6 of Example 50, and steps 2 and 5 of Example 51. Step 3 of Example 51 was replaced by treatment with NaBH4 in EtOH at room temperature to afford racemic material. The title compound was isolated (0.075 g) as a white amorphous powder. LCMS-ESI− (m/z): [M−H]− calcd for C24H24ClO3: 395.14; found: 394.96. 1H-NMR: 400 MHz, (CDCl3) δ: 7.69-7.61 (m, 1H); 7.58 (s, 1H); 7.54 (s, 1H); 7.53-7.46 (m, 2H); 7.30-7.23 (m, 1H); 7.21 (d, J=8.4 Hz, 1H); 7.14 (d, J=8.4 Hz, 1H); 5.27 (s, 2H); 2.56 (s, 3H); 2.48 (s, 3H); 1.01 (s, 9H).
Workup
- custom2-tert-Butoxy-2-(1-(4-chlorophenyl)-3,6-dimethylnaphthalen-2-yl)acetic acid (58) was prepared with a route similar to
- customto afford racemic material
Sources & evidence
- ORD record
- ord-f90c27511fd140edb496f7c5efa9e712
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09102614B2
Reaction notes
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