Iodine → (+)-Sparteine

HRID 1051435Notes

Reaction equation

HRID 1051435 reaction equation
[CH2:1]1[CH2:10][C@@H:9]2[N:4]([CH2:5][C@H:6]3[C@H:13]4[CH2:14][CH2:15][CH2:16][C:17](=O)[N:12]4[CH2:11][C@@H:8]2[CH2:7]3)[CH2:3][CH2:2]1.[BH4-].[Na+].II.[OH-].[OH-].[K+]>C1COCC1.CCOCC>[CH2:1]1[CH2:10][C@H:9]2[N:4]([CH2:5][C@@H:6]3[C@@H:13]4[CH2:14][CH2:15][CH2:16][CH2:17][N:12]4[CH2:11][C@H:8]2[CH2:7]3)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 807IodineHCID 91471(+)-LupanineHCID 4311764Sodium borohydrideHCID 19753598hydroxide KOH

Product 1

HCID 7014(+)-SparteineYield 88%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of Lupanine (49.6 mg) in THF (3 mL) as ether was added NaBH4 (7.6 mg, 1.0 eq) and I2 (25.4 mg, 0.5 eq). The mixture was stirred at 80° C. for 16 hours and then cooled to room temperature. As alcohol MeOH (10 mL) was added and the mixture was subsequently poured into 50 mL of 5% aqueous alkaline hydroxide KOH. The resulting solution was extracted with Et2O (5×40 mL) as organic solvent, the organic extracts were dried over Na2SO4 and then concentrated to afford Sparteine as a colorless oil (41.2 mg, 88% yield).

Workup

  1. temperaturecooled to room temperature
  2. extractionThe resulting solution was extracted with Et2O (5×40 mL) as organic solvent
  3. dry with materialthe organic extracts were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7d6170be1b5f42d49b4484b6bcef49d6
Source dataset
uspto-grants-2016_07
Patent number
US09388182B2

Reaction notes

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