Tetrahydrofuran → 3-[N-BOC-2-(Azetidin-3-yl)ethyl]-2-piperidone

HRID 2209460Notes

Reaction equation

HRID 2209460 reaction equation
[Li+].C[CH:3]([N-:5]C(C)C)C.[C:9]([N:16]1[CH2:19][CH:18]([CH2:20][CH2:21]I)[CH2:17]1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[CH2:23]1[CH2:27][O:26][CH2:25][CH2:24]1>>[C:9]([N:16]1[CH2:19][CH:18]([CH2:20][CH2:21][CH:24]2[CH2:23][CH2:27][CH2:3][NH:5][C:25]2=[O:26])[CH2:17]1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2724682Lithium diisopropylamideHCID 19034125tert-Butyl 3-(2-iodoethyl)azetidine-1-carboxylate

Product 1

HCID 193809363-[N-BOC-2-(Azetidin-3-yl)ethyl]-2-piperidone

Procedure

A solution of 135 (for preparation see; D. H. Hua, et. al., JOC, 55, 3682, 1990) (0.19 g, 1.2 mmol) in THF (3.9 mL) at -78° C. was added LDA (0.58 mL, 1.2 mmol, 2.0M/heptane/THF/ethylbenzene) dropwise. After 15 min 134 (0.30 g, 0.96 mmol) in THF (3.5 mL) was added dropwise. After stirring 1.0 h, the reaction was quenched with CH3OH (7.5 mL) and the resulting solution warmed to ambient temperature. The solution was then diluted with EtOAc and then washed with H2O, 5% KHSO4, sat. NaHCO3, and brine, dried (MgSO4), and concentrated to give 136 (0.27 g) as a white solid. Rf 0.25 (silica, 2:1 CH2Cl2 /acetone).

Workup

  1. customthe reaction was quenched with CH3OH (7.5 mL)
  2. additionThe solution was then diluted with EtOAc
  3. washwashed with H2O, 5% KHSO4, sat. NaHCO3, and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-946d4dcbfbb84237a5bf4133229b2d5e
Source dataset
uspto-grants-1995_10
Patent number
US05455243

Reaction notes

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