Sodium borohydride → benzyl (2R)-5-hydroxy-2-methylpiperidine-1-carboxylate

HRID 81146Notes

Reaction equation

HRID 81146 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][N:3]1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[BH4-].[Na+]>CO>[OH:8][CH:5]1[CH2:4][N:3]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[C@H:2]([CH3:1])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86724499Benzyl (R)-2-methyl-5-oxopiperidine-1-carboxylate

Product 1

HCID 86724500benzyl (2R)-5-hydroxy-2-methylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of benzyl (2R)-2-methyl-5-oxopiperidine-1-carboxylate (365 mg, 1.47 mmol) in methanol (2.9 mL) at 0° C. was added sodium borohydride (84 mg, 2.21 mmol). The reaction mixture was stirred at 0° C. for 1 hour and then stirred for 16 hours at room temperature. The mixture was quenched with saturated aqueous ammonium chloride and concentrated. The resulting residue was extracted with DCM (3×) and the combined extracts were dried over sodium sulfate, filtered, and concentrated to afford benzyl (2R)-5-hydroxy-2-methylpiperidine-1-carboxylate. MS ESI calc'd. for C14H19NO3 [M+H]+ 250. found 250.

Workup

  1. stirringstirred for 16 hours at room temperature
  2. customThe mixture was quenched with saturated aqueous ammonium chloride
  3. concentrationconcentrated
  4. extractionThe resulting residue was extracted with DCM (3×)
  5. dry with materialthe combined extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-348b819400ff47138e52b8c3d8469ccc
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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