Sodium borohydride → HCID 20203547, compound

HRID 1732056Notes

Reaction equation

HRID 1732056 reaction equation
[BH4-].[Na+].[CH2:3]([C:5]1([CH2:22][CH3:23])[CH2:20][CH2:19][N:8]2[C:9]3[C:14]([C:15]([CH3:16])=[C:7]2[C:6]1=[O:21])=[CH:13][C:12]([O:17][CH3:18])=[CH:11][CH:10]=3)[CH3:4]>C(O)C>[CH2:22]([C:5]1([CH2:3][CH3:4])[CH2:20][CH2:19][N:8]2[C:9]3[C:14]([C:15]([CH3:16])=[C:7]2[CH:6]1[OH:21])=[CH:13][C:12]([O:17][CH3:18])=[CH:11][CH:10]=3)[CH3:23]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20203557HCID 20203557, compound

Product 1

HCID 20203547HCID 20203547, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

Sodium borohydride (380 mg, 10 mmol) was added portionwise to a solution of 8,8-diethyl-6,7,8,9-tetrahydro-2-methoxy-10-methylpyrido[1,2-a]indol-9-one (710 mg, 2.5 mmol) in ethanol (50 mL). The reaction mixture was stirred at 25° C. overnight. The solvent was evaporated in vacuo and the residue partitioned between 1% ammonium hydroxide (30 mL) and chloroform (40 mL). The separated organic layer was dried over MgSO4, filtered, and evaporated to afford 530 mg (74%) of the desired alcohol as a light amber oil.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue partitioned between 1% ammonium hydroxide (30 mL) and chloroform (40 mL)
  3. dry with materialThe separated organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-2ec696be0d804760ae0a2a671274a0ac
Source dataset
uspto-grants-1986_11
Patent number
US04624954

Reaction notes

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