Methanol → Benzyl 5-hydroxy-2-methylpiperidine-1-carboxylate

HRID 1749369Notes

Reaction equation

HRID 1749369 reaction equation
C1COCC1.CO.[Li+].[BH4-].[CH3:10][CH:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][N:12]1[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>CC(C)=O>[CH2:21]([O:20][C:18]([N:12]1[CH2:13][CH:14]([OH:17])[CH2:15][CH2:16][CH:11]1[CH3:10])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 71305938Benzyl 2-methyl-5-oxopiperidine-1-carboxylate

Product 1

HCID 71305932Benzyl 5-hydroxy-2-methylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of THF (200 mL) and MeOH (11 mL) was added LiBH4 (2 M, 89 mL, 0.18 mol). Some gas evolution and small exotherm were observed. The reaction was aged at room temperature for 30 min before being cooled to −10° C. with an acetone:ice bath. ±benzyl 2-methyl-5-oxopiperidine-1-carboxylate (22.0 g, 0.089 mol) was then added dropwise, keeping the temperature below −5° C. The reaction was then aged at −10° C. for 30 min. The reaction was quenched by adding half-saturated, aqueous NaHCO3, then extracted with EtOAc. The layers were separated and the organics dried with MgSO4. The organics were concentrated to give the titled compound as a crude, colorless oil.

Workup

  1. customthe temperature below −5° C
  2. waitThe reaction was then aged at −10° C. for 30 min
  3. customThe reaction was quenched
  4. additionby adding half-saturated
  5. extractionaqueous NaHCO3, then extracted with EtOAc
  6. customThe layers were separated
  7. dry with materialthe organics dried with MgSO4
  8. concentrationThe organics were concentrated

Sources & evidence

ORD record
ord-522d2eeaab7c42bca6839abc49fd9316
Source dataset
uspto-grants-2015_10
Patent number
US09156819B2

Reaction notes

Loading…