1-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylate → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

HRID 1457710Notes

Reaction equation

HRID 1457710 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](OCC)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethyl N-t-butyloxycarbonylpiperidine-4-carboxylate (32.34 g, 0.1257 mol) in THF (100 mL) at 0° C. was added dropwise 1M LAH in THF (87.9 mL, 0.0879 mol). After 2 hours, excess hydride was quenched by the addition of water (3.2 mL), 2M NaOH (3.2 mL) and water (10 mL). The mixture was filtered, washed with EtOAc and the filtrate washed with water, sat. NaCl, dried (MgSO4) and concentrated. Pumping to constant weight gave 22.72 g (84%); mp: 79.2°-81.1° C.; 1H NMR (300 MHz, CDCl3) δ 4.12 (bd, J=12.8 Hz 2H), 3.49 (d, J=6.2 Hz, 2H), 2.68 (dt, J=13.2, 1.8 Hz, 2H), 1.69 (m, 3H), 1.44 (s, 9H, overlapped with m, 1H), 1.14 (m, 2H).

Workup

  1. customexcess hydride was quenched by the addition of water (3.2 mL), 2M NaOH (3.2 mL) and water (10 mL)
  2. filtrationThe mixture was filtered
  3. washwashed with EtOAc
  4. washthe filtrate washed with water, sat. NaCl
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customgave 22.72 g (84%)

Sources & evidence

ORD record
ord-af18b1c9c158422e89ea43d74fd75b62
Source dataset
uspto-grants-1998_12
Patent number
US05849736

Reaction notes

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