Cyclohexanone → HCID 59371572, compound

HRID 2095406Notes

Reaction equation

HRID 2095406 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17]1(=O)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[SiH](CC)(CC)CC>C[N+]([O-])=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 12052TriethylsilaneHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

Product 1

HCID 59371572HCID 59371572, compound

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent2×

Procedure

A solution of 1-(tert-butoxycarbonyl)-4-(2-hydroxyethyl)piperidine (229 mg, 1.0 mmol) and cyclohexanone (86 μL, 0.83 mmol) in MeNO2 (2 mL), followed by Et3SiH (160 μL, 1.0 mmol) were added successively to a suspension of FeCl3 (35 mg, 0.20 mmol) in MeNO2 (3 mL) at room temperature under Ar protection. After the mixture was stirred at rt for 112 h, the reaction was quenched by addition of phosphate buffer (pH 7). The mixture was extracted with CH2Cl2, and the organic layer was dried over Na2SO4. After evaporation, the residue was purified by CC (SiO2, hexane/EtOAc 10:1 to 6:1) to afford 1-(tert-butoxycarbonyl)-4-[2-(cyclohexyloxy)ethyl]piperidine together with a with by-product (182 mg total) as a colorless oil. This mixture was used in the following step without further purification.

Workup

  1. customthe reaction was quenched by addition of phosphate buffer (pH 7)
  2. extractionThe mixture was extracted with CH2Cl2
  3. dry with materialthe organic layer was dried over Na2SO4
  4. customAfter evaporation
  5. customthe residue was purified by CC (SiO2, hexane/EtOAc 10:1 to 6:1)

Sources & evidence

ORD record
ord-4377077077084160ad399d992b269527
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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