Phenolate Sodium → 3-(1,3-Dimethylcyclobutanecarbonyloxy)-4-(isovaleryloxy)phenyl tert-butylaminomethyl ketone
Reaction equation
[C:1]([NH:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16](=[O:21])[CH2:17][CH:18]([CH3:20])[CH3:19])=[C:11]([OH:22])[CH:10]=1)=[O:8])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].C1([O-])C=CC=CC=1.[Na+].[CH3:34][C:35]1([C:40](Cl)=[O:41])[CH2:38][CH:37]([CH3:39])[CH2:36]1>>[C:1]([NH:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16](=[O:21])[CH2:17][CH:18]([CH3:19])[CH3:20])=[C:11]([O:22][C:40]([C:35]2([CH3:34])[CH2:38][CH:37]([CH3:39])[CH2:36]2)=[O:41])[CH:10]=1)=[O:8])([CH3:2])([CH3:4])[CH3:3]Participants
5
Reactant 4
Product 1
Procedure
Following a procedure similar to that described in Example 13A above, when 3-hydroxy-4-(isovaleryloxy)phenyl tert-butylaminomethyl ketone is interacted with one equivalent of sodium methoxide and the resulting sodium phenolate salt is reacted with 1,3-dimethylcyclobutanecarbonyl chloride there is obtained 3-(1,3-dimethylcyclobutanecarbonyloxy)-4-(isovaleryloxy)phenyl tert-butylaminomethyl ketone which reacts with hydrochloric acid to yield the hydrochloride salt. When this hydrochloride is catalytically hydrogenated, using the procedure described above in Example 13B, there is obtained 3-(1,3-dimethylcyclobutanecarbonyloxy)-4-(isovaleryloxy)-alpha-(tert-butylaminomethyl)benzyl alcohol hydrochloride.
Sources & evidence
- ORD record
- ord-04aaf9f3ded94811a4defc9d2c3677ff
- Source dataset
- uspto-grants-1980_03
- Patent number
- USRE030241
Reaction notes
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