1-tert-Butyl 3-ethyl 3-benzylpiperidine-1,3-dicarboxylate → HCID 54002145, compound

HRID 970408Notes

Reaction equation

HRID 970408 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:21](OCC)=[O:22])([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([CH2:21][OH:22])([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 196965021-tert-Butyl 3-ethyl 3-benzylpiperidine-1,3-dicarboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 54002145HCID 54002145, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a stirring solution (+/−)-N-(t-butoxycarbonyl)-3-(carboethoxy)-3-(phenylmethyl)-piperidine (200 mg, 0.58 mmol) in dry toluene (20 mL) at −78° C. was added a 1.5 M solution of diisobutylaluminium hydride in toluene (2.0 mL). After 6 h, the reaction was warmed to room temperature and quenched by the addition of 1M HCl (50 mL). The reaction was extracted with EtOAc (4×40 mL). The organic layers were combined, washed with brine, dried over Na2SO4, and conc. in vacuo to an oil. The oil was purified by flash chromatography (SiO2, 7–20% EtOAc in hexanes) to yield 86 mg of the product as a colorless oil. MS (ESI) 306 (M+H).

Workup

  1. customquenched by the addition of 1M HCl (50 mL)
  2. extractionThe reaction was extracted with EtOAc (4×40 mL)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customThe oil was purified by flash chromatography (SiO2, 7–20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-88617ed85c78494ebfaf64ef253c87dd
Source dataset
uspto-grants-2007_12
Patent number
US07312222B2

Reaction notes

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