Sodium borohydride → HCID 13749192, compound

HRID 1732058Notes

Reaction equation

HRID 1732058 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]1[CH2:11][CH2:12][CH2:13][C:14](=[O:15])[C:6]1=[C:5]2[CH3:16].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]1[CH2:11][CH2:12][CH2:13][CH:14]([OH:15])[C:6]1=[C:5]2[CH3:16]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13376760HCID 13376760, compound

Product 1

HCID 13749192HCID 13749192, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-bromo-10-methyl-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-one (5.56 g, 20 mmol, described in Example 17, Step 1), in methanol (350 mL) was added sodium borohydride (2.5 g) portionwise, upon cooling. The reaction mixture was stirred at room temperature for 1 hour, and evaporated. The residue was partitioned between water and methylene chloride, the organic layer separated, dried (MgSO4), filtered, and evaporated to obtain the title compound 3.4 g (61%) m.p. 120°-123° C.

Workup

  1. temperatureupon cooling
  2. customevaporated
  3. customThe residue was partitioned between water and methylene chloride
  4. customthe organic layer separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-970d07224030430497040fc2cb2f75cc
Source dataset
uspto-grants-1986_11
Patent number
US04624954

Reaction notes

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