Sodium borohydride → 6-methoxy-1-[2-(4-trifluoromethyl-phenyl)-ethyl]-2,3,4,9-tetrahydro-1H-beta-carboline

HRID 563918Notes

Reaction equation

HRID 563918 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]1[C:10]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)=[N:9][CH2:8][CH2:7][C:6]2=1.[BH4-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]1[CH:10]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)[NH:9][CH2:8][CH2:7][C:6]2=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 1362075296-Methoxy-1-[2-(4-trifluoromethyl-phenyl)-ethyl]-4,9-dihydro-3H-beta-carboline

Product 1

HCID 598200086-methoxy-1-[2-(4-trifluoromethyl-phenyl)-ethyl]-2,3,4,9-tetrahydro-1H-beta-carboline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 91 mg (0.24 mmol) 6-methoxy-1-[2-(4-trifluoromethyl-phenyl)-ethyl]-4,9-dihydro-3H-β-carboline and 27.7 mg (0.73 mmol) sodium borohydride in 5 mL ethanol was stirred for 2 h at room temperature. The mixture was filtered and evaporated to dryness. Trituration with ethyl acetate yielded after drying 90 mg (98%) of the title compound as light yellow solid.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated to dryness
  3. customTrituration with ethyl acetate yielded
  4. dry with materialafter drying 90 mg (98%) of the title compound as light yellow solid

Sources & evidence

ORD record
ord-e1ace71666b540e5bf8af55a84321cb7
Source dataset
uspto-grants-2011_11
Patent number
US08067598B2

Reaction notes

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