Sodium borohydride → HCID 20203555, compound

HRID 978711Notes

Reaction equation

HRID 978711 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]2[CH2:13][CH2:14][C:15]([CH2:21][CH:22]=[CH2:23])([CH2:18][CH:19]=[CH2:20])[C:16](=[O:17])[C:5]=12>C(O)C>[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]2[CH2:13][CH2:14][C:15]([CH2:18][CH:19]=[CH2:20])([CH2:21][CH:22]=[CH2:23])[CH:16]([OH:17])[C:5]=12

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20203548HCID 20203548, compound

Product 1

HCID 20203555HCID 20203555, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (10.53 g, 270 mmol) was added portionwise upon cooling to a solution of 6,7,8,9-tetrahydro-10-methyl-8,8-bis(2-propenyl)pyrido[1,2-a]indol-9-one (12.8 g, 45.8 mmol), in ethanol (350 mL) at 25° C. The reaction mixture was stirred at room temperature for 24 hours. The solvent was removed in vacuo to near-dryness, and the residue partitioned between water (300 mL) and ether (300 mL). The separated organic layer was washed with brine (100 mL), dried over MgSO4, filtered and evaporated to afford 12.63 g (98%) of the title compound as a light amber oil.

Workup

  1. customThe solvent was removed in vacuo to near-dryness
  2. customthe residue partitioned between water (300 mL) and ether (300 mL)
  3. washThe separated organic layer was washed with brine (100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-09f3d6bed70d4f5888e7733386c63d03
Source dataset
uspto-grants-1987_05
Patent number
US04665183

Reaction notes

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