Sodium borohydride → 2-(Dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridine-3-methanol

HRID 1777887Notes

Reaction equation

HRID 1777887 reaction equation
[CH3:1][O:2][CH:3]([O:16][CH3:17])[C:4]1[C:13]([CH:14]=[O:15])=[CH:12][C:11]2[CH2:10][CH2:9][CH2:8][NH:7][C:6]=2[N:5]=1.[BH4-].[Na+]>CO.C(Cl)Cl>[CH3:17][O:16][CH:3]([O:2][CH3:1])[C:4]1[C:13]([CH2:14][OH:15])=[CH:12][C:11]2[CH2:10][CH2:9][CH2:8][NH:7][C:6]=2[N:5]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 1180364262-(Dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridine-3-carbaldehyde2×

Product 1

HCID 1180364762-(Dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridine-3-methanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridine-3-carbaldehyde (intermediate 41, 10 g, 38.2 mmol) in MeOH (120 ml) and DCM (60 ml) was added NaBH4 (1.16 g, 30.6 mmol). The reaction mixture was stirred at room temperature for 30 min, then slowly quenched with sat. aq. NH4Cl and concentrated until the organic solvents had been mostly removed. The resulting mixture was extracted with DCM (4×). The combined organic phases were dried over

Workup

  1. customslowly quenched with sat. aq. NH4Cl
  2. concentrationconcentrated until the organic solvents
  3. customhad been mostly removed
  4. extractionThe resulting mixture was extracted with DCM (4×)
  5. customThe combined organic phases were dried over

Sources & evidence

ORD record
ord-1732d9ba4de849ea87245e76143ffac1
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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