Potassium sodium tartarate → HCID 58017293, compound

HRID 661565Notes

Reaction equation

HRID 661565 reaction equation
C[O:2][C:3]([C:5]1([CH2:20][CH2:21][CH3:22])[CH2:11][CH2:10][CH:9]2[N:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:6]1[CH2:7][CH2:8]2)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>O1CCCC1>[C:16]([O:15][C:13]([N:12]1[CH:9]2[CH2:8][CH2:7][CH:6]1[C:5]([CH2:3][OH:2])([CH2:20][CH2:21][CH3:22])[CH2:11][CH2:10]2)=[O:14])([CH3:18])([CH3:19])[CH3:17]

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarate2×HCID 21226445Aluminium lithium hydrideHCID 58017255HCID 58017255, compound

Product 1

HCID 58017293HCID 58017293, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

2-Propyl-8-aza-bicyclo[3.2.1]octane-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester (mixture of endo and exo isomers from Step 6, 0.98 g, 3.1 mmol) was dissolved in tetrahydrofuran (15 mL), and the resulting mixture was cooled to 0° C. A solution of lithium aluminum hydride in tetrahydrofuran (1 M, 3.3 mL, 3.3 mmol) in tetrahydrofuran was added dropwise over 10 minutes, and stirring was continued at 0° C. for 1.5 hours. A saturated aqueous solution of potassium sodium tartrate (10 mL) was added, and the mixture was warmed to room temperature and stirred for 15 hours. Additional saturated aqueous solution of potassium sodium tartrate (10 mL) was added, and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, ethyl acetate/hexane) to provide 2-hydroxymethyl-2-propyl-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester as a separable mixture of endo and exo isomers, both as colorless oils (0.68 g and 0.17 g, 76% and 19% yield, respectively).

Workup

  1. temperaturethe mixture was warmed to room temperature
  2. stirringstirred for 15 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-85277096cc154c34b617e6f9c024a0fe
Source dataset
uspto-grants-2011_12
Patent number
US08084623B2

Reaction notes

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