Sodium borohydride → HCID 20203549, compound

HRID 1732053Notes

Reaction equation

HRID 1732053 reaction equation
[BH4-].[Na+].[CH2:3]([C:5]1([CH2:20][CH3:21])[CH2:18][CH2:17][N:8]2[C:9]3[C:14]([C:15]([CH3:16])=[C:7]2[C:6]1=[O:19])=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:4]>CO>[CH2:20]([C:5]1([CH2:3][CH3:4])[CH2:18][CH2:17][N:8]2[C:9]3[C:14]([C:15]([CH3:16])=[C:7]2[CH:6]1[OH:19])=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:21]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20203543HCID 20203543, compound

Product 1

HCID 20203549HCID 20203549, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

Sodium borohydride (19 g, 500 mmol) was added portionwise upon cooling to a solution 8,8-diethyl-6,7,8,9-tetrahydro-10-methylpyrido[1,2-a]indol-9-one (12.8 g, 50 mmol) in methanol (500 mL) at 25° C. The reaction mixture was heated at 40° C. for 18 hours. The solvent was removed in vacuo and the residue partitioned between 1% ammonium hydroxide (100 mL) and chloroform (120 mL). The separated organic layer was dried over MgSO4, filtered and evaporated to afford the desired alcohol 12 g, (93%) as a greenish oil.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between 1% ammonium hydroxide (100 mL) and chloroform (120 mL)
  3. dry with materialThe separated organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-b53890fc3e8741c4a07ce1fc4356dfff
Source dataset
uspto-grants-1986_11
Patent number
US04624954

Reaction notes

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