Diisopropylethylamine → 4-(4-Bromophenyl)-1-(oxetan-3-yl)piperidine

HRID 2209103Notes

Reaction equation

HRID 2209103 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[O:23]1[CH2:26][C:25](=O)[CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][N:11]([CH:25]3[CH2:26][O:23][CH2:24]3)[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27571594-(4-Bromophenyl)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 150242543-Oxetanone

Product 1

HCID 1178437314-(4-Bromophenyl)-1-(oxetan-3-yl)piperidineYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a round-bottomed, single-necked, 100-mL flask were placed 4-(4-bromophenyl)piperidine (500.0 mg, 2.08 mmol), N,N-diisopropylethylamine (0.36 mL, 2.08 mmol), 3-oxetanone (0.27 mL, 4.16 mmol), and sodium triacetoxyborohydride (1544.5 mg, 7.3 mmol) in THF (15 mL). The mixture was stirred at room temperature for 16 h. Then, it was quenched with water and the organic layers extracted with EtOAc (3×5 mL). The combined organic layers were washed with water (2×5 mL) and brine (1×5 mL), dried (Na2SO4), concentrated, and purified by flash chromatography (100% Hexane to 100% EtOAc) to give 350.0 mg (57%) of 4-(4-bromophenyl)-1-(oxetan-3-yl)piperidine.

Workup

  1. customIn a round-bottomed, single-necked, 100-mL flask were placed
  2. customThen, it was quenched with water
  3. extractionthe organic layers extracted with EtOAc (3×5 mL)
  4. washThe combined organic layers were washed with water (2×5 mL) and brine (1×5 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified by flash chromatography (100% Hexane to 100% EtOAc)

Sources & evidence

ORD record
ord-73ebde737e244788adb7866841dbbbeb
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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