Sodium Hydroxide → (S)-1-(3,4,5-trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidine

HRID 323221Notes

Reaction equation

C([C@](C(O)=O)(O)[C@](C(=O)C1C=CC(OC)=CC=1)(O)C(O)=O)(=O)C1C=CC(OC)=CC=1.[Cl:31][C:32]1[CH:33]=[C:34]([C@@:39]2([CH2:44][CH2:45][OH:46])[CH2:43][CH2:42][NH:41][CH2:40]2)[CH:35]=[CH:36][C:37]=1[Cl:38].[OH-].[Na+].C(=O)(O)[O-].[Na+].[CH3:54][O:55][C:56]1[CH:57]=[C:58]([CH:62]=[C:63]([O:67][CH3:68])[C:64]=1[O:65][CH3:66])[C:59](Cl)=[O:60]>CC(C)=O.O>[CH3:68][O:67][C:63]1[CH:62]=[C:58]([CH:57]=[C:56]([O:55][CH3:54])[C:64]=1[O:65][CH3:66])[C:59]([N:41]1[CH2:42][CH2:43][C@@:39]([C:34]2[CH:35]=[CH:36][C:37]([Cl:38])=[C:32]([Cl:31])[CH:33]=2)([CH2:44][CH2:45][OH:46])[CH2:40]1)=[O:60]

Participants

Conditions

Temperature: 0 °C

Procedure

Combine (S)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt (6.0 g, 8.84 mmol) acetone (40 mL), water (40 mL), sodium hydroxide (0.335 g, 8.87 mmol), and sodium bicarbonate (3.73 g, 8.87 mmol). Cool to about 0° C. Add a solution of 3,4,5-trimethoxybenzoyl chloride (2,2 g, 9.7 mmol) in acetone (12 mL) over about 15 minutes. After 3 hours, partition the reaction mixture between ethyl acetate and brine. Extract the organic layer with 1 M sodium hydroxide solution, saturated sodium bicarbonate solution, 1 M hydrochloric acid solution, then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give the title compound: Rf=0.11 (silica gel, ethyl acetate).

Workup

custompartition the reaction mixture between ethyl acetate and brine
extractionExtract the organic layer with 1 M sodium hydroxide solution, saturated sodium bicarbonate solution, 1 M hydrochloric acid solution
dry with materialDry the organic layer over MgSO4
filtrationfilter
customevaporate in vacuo

Sources & evidence

ORD record: ord-061e00af159d47d786ae57ab9ed1969d
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211199B1

Reaction notes

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