Methanol → 1-Benzyloxycarbonyl-3-hydroxymethyl-1,2,5,6-tetrahydropyridine

HRID 258389Notes

Reaction equation

HRID 258389 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]=[C:13]([C:17](OC)=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C.CO.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]=[C:13]([CH2:17][OH:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 18797103Methyl 1-benzyloxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylate

Product 1

HCID 200899311-Benzyloxycarbonyl-3-hydroxymethyl-1,2,5,6-tetrahydropyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the compound of step 1 (2.0 g, 7.33 mmol) in tetrahydrofuran (30 ml) at -20° C. was added DIBAL-H. The mixture was warmed up to 0° C. and stirred at this temperature for 5 hours. Addition of methanol (5 ml) at 0° C. followed by addition of a saturated solution of Rochelle salt (10 ml) resulted in the formation of a white slurry. After stirring for an additional 2 hours, this was filtered; the filtrate was extracted with ether and the organic layer was washed with brine and dried over magnesium sulfate. Upon evaporation, the title compound was obtained as a slightly yellow oil (1.14 g, 4.6 mmol, 63% yield).

Workup

  1. customresulted in the formation of a white slurry
  2. stirringAfter stirring for an additional 2 hours
  3. filtrationthis was filtered
  4. extractionthe filtrate was extracted with ether
  5. washthe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customUpon evaporation

Sources & evidence

ORD record
ord-1dd250861368497ab2e51083c1fb67ed
Source dataset
uspto-grants-1993_11
Patent number
US05266569

Reaction notes

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