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

HRID 1198504Notes

Reaction equation

HRID 1198504 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). 1H ITMR (400 MHz, CDCl3) δ 5.81 (bs, 1H), 3.95 (m, 2H), 3.54 (m, 2H), 3.10 (m, 2H), 2.47 (m, 1H), 2.26 (m, 1H), 2.00-1.40 (m, 8H), 1.43 (s, 9H). ##STR60##

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-9e40ad7eeb6d46dd809465c3dda55e9a
Source dataset
uspto-grants-1994_01
Patent number
US05281585

Reaction notes

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