Potassium sodium tartarate → HCID 72338937, compound

HRID 1873537Notes

Reaction equation

HRID 1873537 reaction equation
[CH3:1][N:2]([CH3:22])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([C:20]#N)([CH2:13][CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:12][CH:7]2[CH2:6]1)=[O:4].[H-].C([Al+]CC(C)C)C(C)C.C(C(C(C([O-])=O)O)O)([O-])=[O:34].[Na+].[K+]>ClCCl>[CH3:1][N:2]([CH3:22])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([CH2:13][CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)([CH:20]=[O:34])[CH2:12][CH:7]2[CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21225700DiisobutylaluminumhydrideHCID 686262975-Cyano-5-cyclohexylmethyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide

Product 1

HCID 72338937HCID 72338937, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Upon cooling to 0° C. by an ice-water bath, 5-cyano-5-cyclohexylmethyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 15a (1.2 g, 3.95 mmol) was dissolved in 30 mL of dichloromethane with stirring followed by dropwise addition of diisobutylaluminium hydride (11.8 mL, 11.8 mmol). The reaction mixture was reacted for 1 hour. The reaction was monitored by TLC until the disappearance of the starting materials. Then a solution of saturated aqueous potassium sodium tartrate was added. The mixture was stirred until the solution was clear and extracted with ethyl acetate (100 mL×3). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 5-cyclohexylmethyl-5-formyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 15b (0.4 g, yield 33%) as a light yellow oil.

Workup

  1. customThe reaction mixture was reacted for 1 hour
  2. stirringThe mixture was stirred until the solution
  3. extractionextracted with ethyl acetate (100 mL×3)
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f9cf4e5feba74d34831a211f4b8fa161
Source dataset
uspto-grants-2012_11
Patent number
US08304411B2

Reaction notes

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