Acetic Acid → HCID 19789780, compound

HRID 1656107Notes

Reaction equation

HRID 1656107 reaction equation
[BH4-].[Na+].[CH2:3]([N:5]1[CH2:17][CH2:16][CH:15]2[CH:7]([NH:8][C:9]3[C:14]2=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:6]1)[CH3:4].[C:18](O)(=O)[CH3:19]>>[CH2:3]([N:5]1[CH2:17][CH2:16][CH:15]2[CH:7]([N:8]([CH2:18][CH3:19])[C:9]3[C:14]2=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:6]1)[CH3:4]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydride2×HCID 19789750HCID 19789750, compound

Product 1

HCID 19789780HCID 19789780, compound

Procedure

NaBH4 (1.08 g) was added under ice-cooling to a solution of 2-ethyl-1,2,3,4,4a,9a-hexahydro-pyrido[3,4-b]indole (1.16 g) in 40 ml of acetic acid. After stirring the solution at room temperature for 4 hrs, additional NaBH4 (0.54 g) was added and the mixture was stirred for 3 hrs. After removal of acetic acid by evaporation, the residue was neutralized with ammonia, extracted with ethyl acetate, washed with brine and dried over magnesium sulfate. The solvent was evaporated off, thereby affording 1.26 g of the title compound as a pale yellow oil.

Workup

  1. stirringthe mixture was stirred for 3 hrs
  2. customAfter removal of acetic acid
  3. customby evaporation
  4. extractionextracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated off

Sources & evidence

ORD record
ord-c47fafc96c4e40bca01b51820d8e3c6e
Source dataset
uspto-grants-1993_10
Patent number
US05252580

Reaction notes

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