Sodium Hydroxide → (S)-1-(3,3-diphenylpropyl)-3-methylpyrrolidin-3-ol

HRID 1496694Notes

Reaction equation

COC(C1[C@H](C2C=CC=C([N+]([O-])=O)C=2)C(C(O)=O)=C(C)NC=1C)=O.[C:25]1([CH:31]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:32][CH2:33][N:34]2[CH2:38][CH2:37][C:36]([CH3:40])([OH:39])[CH2:35]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[OH-].[Na+]>C(O)(C)C>[C:41]1([CH:31]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:32][CH2:33][N:34]2[CH2:38][CH2:37][C@:36]([CH3:40])([OH:39])[CH2:35]2)[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

Conditions

Temperature: 30 °C

Procedure

According to Example 15, (R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid and 1-(3,3-diphenylpropyl)-3-methylpyrrolidin-3-ol were synthesized. To a solution of D-bis(paramethylbenzoyl)tartaric acid ((+)-Di-1,4-toluoyl-D-tartaric acid) (280 g, 0.7 mol) in isopropanol (300 mL) was added a solution of 1-(3,3-diphenylpropyl)-3-methylpyrrolidin-3-ol (280 g, 0.95 mol) in isopropanol (300 mL) at 90° C. After the solution became clear, the solution was cooled down to 30° C. slowly, and filtered to produce a white solid, which was treated with sodium hydroxide to produce (S)-1-(3,3-diphenylpropyl)-3-methylpyrrolidin-3-ol (52 g) in a yield of 18.6%.

Workup

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Sources & evidence

ORD record: ord-8c00b2587dd3453e8ed0bb101ea93ed9
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09198902B2

Reaction notes

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