Sodium Bicarbonate → (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)octadecahydro-1H-cyclopenta[a]chrysen-9(5bH)-one

HRID 1401000Notes

Reaction equation

HRID 1401000 reaction equation
[Cl-].[CH3:2][C@:3]12[C@@:20]3([CH3:21])[C@@H:11]([C@:12]4([CH3:25])[C@@H:17]([CH2:18][CH2:19]3)[C:16]([CH3:23])([CH3:22])[C:15](=[O:24])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C@@H:8]1[C@H:7]1[C@H:26]([C:29]([CH3:31])=[CH2:30])[CH2:27][CH2:28][C@:6]1([NH3+:32])[CH2:5][CH2:4]2.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[NH2:32][C@:6]12[CH2:28][CH2:27][C@@H:26]([C:29]([CH3:31])=[CH2:30])[C@@H:7]1[C@@H:8]1[C@@:3]([CH3:2])([CH2:4][CH2:5]2)[C@@:20]2([CH3:21])[C@@H:11]([C@:12]3([CH3:25])[C@@H:17]([CH2:18][CH2:19]2)[C:16]([CH3:22])([CH3:23])[C:15](=[O:24])[CH2:14][CH2:13]3)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 86692354(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-3a-aminium chloride

Product 1

HCID 86692310(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)octadecahydro-1H-cyclopenta[a]chrysen-9(5bH)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-3a-aminium chloride (462 mg, 1.000 mmol) in DCM (6 mL) was added saturated solution of sodium bicarbonate 10 mL. The 2-phase mixture was vigorously stirred, DCM layer separated, it was washed with another portion of 6 mL of saturated sodium bicarbonate solution. The mixture was extracted with 10 mL DCM three times. The combine DCM fractions was finally washed with 5 mL DI water. Upon evaporation and drying, a thick semi-solid was isolated. This crude material was used in the next step without further purification.

Workup

  1. customDCM layer separated
  2. washit was washed with another portion of 6 mL of saturated sodium bicarbonate solution
  3. extractionThe mixture was extracted with 10 mL DCM three times
  4. washThe combine DCM fractions was finally washed with 5 mL DI water
  5. customUpon evaporation
  6. customdrying
  7. customa thick semi-solid was isolated
  8. customThis crude material was used in the next step without further purification

Sources & evidence

ORD record
ord-bd6bf5396f9b40f987436c826d1e4d02
Source dataset
uspto-grants-2014_12
Patent number
US08906889B2

Reaction notes

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