Diisobutylaluminum hydride → Tert-butyl 3-(hydroxymethyl)-4-methylpiperidine-1-carboxylate

HRID 2204504Notes

Reaction equation

HRID 2204504 reaction equation
CC(C[AlH]CC(C)C)C.[CH3:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]1[C:24](OC)=[O:25]>C1COCC1>[OH:25][CH2:24][CH:12]1[CH:11]([CH3:10])[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:13]1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 575191641-Tert-butyl 3-methyl 4-methylpiperidine-1,3-dicarboxylate

Product 1

HCID 58009921Tert-butyl 3-(hydroxymethyl)-4-methylpiperidine-1-carboxylateYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIBAL-H (1 M in toluene, 27.3 mL, 27.3 mmol) was added drop-wise to a solution of 1-tert-butyl 3-methyl 4-methylpiperidine-1,3-dicarboxylate (3.35 g, 13.02 mmol, prepared using R from Preparation #Y.1 and P) in THF (40 mL) at about 0° C. The reaction mixture was stirred for about 1 h before quenching with 10% aqueous potassium sodium tartrate solution in water (50 mL). The reaction mixture was allowed to stir for about 1 h before it was concentrated under reduced pressure. The residue was partitioned with EtOAc (200 mL) and brine (3×100 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to constant weight to afford tert-butyl 3-(hydroxymethyl)-4-methylpiperidine-1-carboxylate as a clear oil (2.58 g, 86%): LC/MS (Table 2, Method a) Rt=2.10 min; MS m/z: 230 (M+H)+.

Workup

  1. custombefore quenching with 10% aqueous potassium sodium tartrate solution in water (50 mL)
  2. stirringto stir for about 1 h before it
  3. concentrationwas concentrated under reduced pressure
  4. customThe residue was partitioned with EtOAc (200 mL) and brine (3×100 mL)
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to constant weight

Sources & evidence

ORD record
ord-4b715d1c5fc54fa495fd8e4b592c099d
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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