Sodium borohydride → 2-(4-fluorobenzyl)-4-(hydroxymethyl)-10-methoxy-8-methyl-7,8-dihydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione

HRID 494125Notes

Reaction equation

HRID 494125 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]3[C:14]([O:23][CH3:24])=[C:15]4[C:20](=[O:21])[N:19]([CH3:22])[CH2:18][CH2:17][N:16]4[C:10]=3[C:9]([C:25](OC)=[O:26])=[N:8]2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]3[C:14]([O:23][CH3:24])=[C:15]4[C:20](=[O:21])[N:19]([CH3:22])[CH2:18][CH2:17][N:16]4[C:10]=3[C:9]([CH2:25][OH:26])=[N:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 68865248Methyl 2-(4-fluorobenzyl)-10-methoxy-8-methyl-1,9-dioxo-1,2,6,7,8,9-hexahydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-4-carboxylate

Product 1

HCID 688646802-(4-fluorobenzyl)-4-(hydroxymethyl)-10-methoxy-8-methyl-7,8-dihydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 2-(4-fluorobenzyl)-10-methoxy-8-methyl-1,9-dioxo-1,2,6,7,8,9-hexahydropyrazino[1′,2′:1,5]pyrrolo[2,3-d]pyridazine-4-carboxylate (0.10 g, 0.24 mmol) in methanol (4 mL) was treated with sodium borohydride (9 mg, 0.24 mmol). After stirring at room temperature for 30 minutes, the reaction mixture was concentrated under vacuum to half the volume. The white solid precipitated was filtered and air dried to provide the title alcohol.

Workup

  1. concentrationthe reaction mixture was concentrated under vacuum to half the volume
  2. customThe white solid precipitated
  3. filtrationwas filtered
  4. customair dried

Sources & evidence

ORD record
ord-084a15db01844241b3cd0c7424b958c9
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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