Ethanol → (S)-3-bromo-5-(1-methylpyrrolidin-2-yl)pyridine (2R,3R)-2,3-bis(benzoyloxy) succinate

HRID 623836Notes

Reaction equation

HRID 623836 reaction equation
[OH2:1].C([C@@:10]([C:25]([OH:27])=[O:26])([OH:24])[C@@:11](C(=O)C1C=CC=CC=1)([OH:15])[C:12]([OH:14])=[O:13])(=O)C1C=CC=CC=1.[Br:28][C:29]1[CH:30]=[N:31][CH:32]=[C:33]([C@@H:35]2[CH2:39][CH2:38][CH2:37][N:36]2[CH3:40])[CH:34]=1.[CH2:41]([OH:43])[CH3:42]>>[C:41]([O:15][C@H:11]([C@@H:10]([O:24][C:34](=[O:1])[C:33]1[CH:32]=[CH:37][CH:38]=[CH:39][CH:35]=1)[C:25]([OH:27])=[O:26])[C:12]([OH:14])=[O:13])(=[O:43])[C:42]1[CH:39]=[CH:35][CH:33]=[CH:34][CH:29]=1.[Br:28][C:29]1[CH:30]=[N:31][CH:32]=[C:33]([C@@H:35]2[CH2:39][CH2:38][CH2:37][N:36]2[CH3:40])[CH:34]=1

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 10633832Pyridine, 3-bromo-5-[(2S)-1-methyl-2-pyrrolidinyl]-HCID 130366077Dibezoyl-L-tartaric acid monohydrate

Product 1

HCID 15355480(S)-3-bromo-5-(1-methylpyrrolidin-2-yl)pyridine (2R,3R)-2,3-bis(benzoyloxy) succinateYield 84%

Procedure

A solution of (−)-dibenzoyl-L-tartaric acid monohydrate (2.11 g, 5.89 mmol, 1.0 equiv) in ethanol (22 mL) was added to (S)-3-bromo-5-(1-methylpyrrolidin-2-yl)pyridine (III) (5.88 mmol, 1.0 equiv) dissolved in ethanol (22 mL) at 20° C. Solids precipitated and the mixture was granulated 18 hours. The light yellow solids filtered from the mixture were washed with ethanol and dried on the filter, giving (S)-3-bromo-5-(1-methylpyrrolidin-2-yl)pyridine (2R,3R)-2,3-bis (benzoyloxy) succinate (IIIB) (2.9556 g, 84%, 99.5% ee).

Workup

  1. customSolids precipitated
  2. filtrationThe light yellow solids filtered from the mixture
  3. washwere washed with ethanol
  4. customdried on the filter

Sources & evidence

ORD record
ord-ae706eab1e1346e09c7f8214577a494e
Source dataset
uspto-grants-2016_04
Patent number
US09303013B2

Reaction notes

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