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

HRID 81144Notes

Reaction equation

HRID 81144 reaction equation
C1COCC1.[Li+].[BH4-].[CH3:8][CH:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][N:10]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>CO>[CH2:19]([O:18][C:16]([N:10]1[CH2:11][CH:12]([OH:15])[CH2:13][CH2:14][CH:9]1[CH3:8])=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 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 887MethanolSolvent

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 a small exotherm were observed. The reaction was aged at room temperature for 30 min before being cooled to −10° C.±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 crude ±benzyl-5-hydroxy-2-methylpiperidine-1-carboxylate as a crude, colorless oil.

Workup

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

Sources & evidence

ORD record
ord-dd14bb1e7ee84e85b163371b2140c2fa
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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