Benzoclidine → HCID 131727932, compound

HRID 2242843Notes

Reaction equation

HRID 2242843 reaction equation
[C:1]([O:9][CH:10]1[CH:15]2[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]2)[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]([OH:27])(=[O:26])[C@@H:19]([C@H:21]([C:23]([OH:25])=[O:24])[OH:22])[OH:20]>CCO>[C:1]([O:9][C@@H:10]1[CH:15]2[CH2:14][CH2:13][N:12]([CH2:17][CH2:16]2)[CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[C:23]([C@@H:21]([C@H:19]([C:18]([O-:27])=[O:26])[OH:20])[OH:22])([O-:25])=[O:24]

Participants

4

Reactant 2

HCID 65630BenzoclidineHCID 444305L-Tartaric acid

Product 1

HCID 131727932HCID 131727932, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(+/−)-3-Quinuclidinol benzoate (Sigma, 17.9 g, 77.5 mmol) was treated with L-tartaric acid (Aldrich, 99% ee, 11.63 g, 77.5 mmol) in EtOH (80%, 222 mL) at ambient temperature for 1 week. The white solid was filtered off and dried under reduced pressure. 6.5 g of 3-(R)-quinuclidinol benzoate·(L)-tartrate was obtained with ˜80% ee (assayed by HPLC. HPLC conditions: chiralpak AD column 25 cm×4 mm ID. solvent, EtOH:hexanes=15:85. flow rate, 1 mL/min. uv, 220 nm. Retention time: (S)-3-quinuclidinol benzoate, 7.87 min; (R)-3-quinuclidinol benzoate 13.3 min.) Recrystallization of the above solid in EtOH (80%, 35 mL) gave the title product (4.5 g, yield, 15%, >98% ee). MS (DCI/NH3) m/z 232 (M+H)+.

Workup

  1. filtrationThe white solid was filtered off
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-dce457631d4f486c9b37e93101bb4017
Source dataset
uspto-grants-2010_03
Patent number
US07674794B2

Reaction notes

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