Nitrogen → HCID 131734058, compound

HRID 714216Notes

Reaction equation

HRID 714216 reaction equation
N#N.C([O:5][C:6](=O)[CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]1[F:21])C.CC(C[AlH]CC(C)C)C.[OH-].[Na+]>C1COCC1.C1(C)C=CC=CC=1.O>[F:21][C@H:9]1[C@@H:8]([CH2:7][CH2:6][OH:5])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]1

Participants

8

Reactant 4

HCID 947NitrogenHCID 14487Diisobutylaluminum hydride2×HCID 14798Sodium HydroxideHCID 23512083HCID 23512083, compound

Product 1

HCID 131734058HCID 131734058, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to an ice-cold solution of tert-butyl 4-(2-ethoxy-2-oxoethyl)-3-fluoropiperidine-1-carboxylate (348 mg, 1.20 mmol) in dry THF (9 mL) was added DIBAL-H (2.41 mL of a 1M solution in toluene, 2.41 mmol). The reaction mixture was stirred at rt for 2 h. DIBAL-H (0.60 mL of a 1M solution in toluene, 0.60 mmol) was added again and the reaction mixture further stirred at rt for 1 h before being cooled to 0° C. Water (0.15 mL) was added followed by aq. 2N NaOH (0.30 mL). The mixture was stirred for 20 min, filtered through celite, washed with EA and concentrated under reduced pressure. The crude residue was purified by FC (hept-EA, 7:3→1:1) to give the title compound as a colorless oil. LC-MS-conditions 08: tR=0.69 min; [M-CH3+H]+=233.35.

Workup

  1. stirringthe reaction mixture further stirred at rt for 1 h
  2. temperaturebefore being cooled to 0° C
  3. stirringThe mixture was stirred for 20 min
  4. filtrationfiltered through celite
  5. washwashed with EA
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by FC (hept-EA, 7:3→1:1)

Sources & evidence

ORD record
ord-d46c42f8ac4046ecafccb067924b77c1
Source dataset
uspto-grants-2015_11
Patent number
US09187435B2

Reaction notes

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