Dimethylformamide → HCID 88851134, compound

HRID 388215Notes

Reaction equation

HRID 388215 reaction equation
OC[C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1/[N+:9](/[O-:12])=[N:10]/[O-:11].[Na+].Br[CH2:15][CH2:16][CH2:17][CH3:18].CN([CH:22]=[O:23])C>>[CH2:15]([O:11]/[N:10]=[N+:9](\[N:4]1[CH2:3][CH2:8][CH:7]([CH2:22][OH:23])[CH2:6][CH2:5]1)/[O-:12])[CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8002Butyl bromideHCID 140590823HCID 140590823, compound

Product 1

HCID 88851134HCID 88851134, compound

Conditions

Temperature
100 °C

Procedure

A suspension of sodium (2S)-2-(hydroxymethyl)-1-[(Z)-oxido-NNO-azoxy]piperidine (1.04 g, 5.27 mmol) and 1-bromobutane (681 μL, 6.33 mmol) in DMF (5 mL) was stirred at 100° C. for 30 min in a microwave reactor. After cooling to rt, the mixture was partitioned between Et2O (50 mL) and brine (50 mL). The organic layer was separated and washed with brine (2×50 mL), dried over MgSO4 and concentrated. The residue was purified by flash chromatography (Biotage 40+M) using 40-50% EtOAc in hexanes gradient, affording the title product: 1H NMR (500 MHz, CDCl3) δ 4.23 (t, 6.9 Hz, 2H), 3.82-3.78 (m, 2H), 3.53 (d, J=6.4, Hz, 2H), 2.95 (dt, J=2.5, 11.9 Hz, 2H), 1.90 (d, J=7.1 Hz, 2H), 1.77-1.71 (m, 2H), 1.65 (m, 2H), 1.50-1.40 (m, 4H), 0.94 (t, J=7.5 Hz, 3H).

Workup

  1. temperatureAfter cooling to rt
  2. customthe mixture was partitioned between Et2O (50 mL) and brine (50 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (2×50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (Biotage 40+M)

Sources & evidence

ORD record
ord-31523946aedf4105bd83de42c569f065
Source dataset
uspto-grants-2013_02
Patent number
US08377911B2

Reaction notes

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