Water → HCID 60134586, compound

HRID 2061089Notes

Reaction equation

HRID 2061089 reaction equation
[N:1]([C:4]([CH3:10])([CH3:9])[CH2:5][C:6](Cl)=[O:7])=[N+:2]=[N-:3].[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.O>ClCCCl>[N:1]([C:4]([CH3:10])([CH3:9])[CH2:5][C:6]([N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:7])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 31268PyrrolidineHCID 601345073-Azido-3-methylbutanoyl chloride

Product 1

HCID 60134586HCID 60134586, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred ice cold solution of 3-azido-3-methylbutanoyl chloride (6.00 g, 37.1 mmol) in anhydrous DCE (100 mL) was added pyrrolidine (6.19 mL, 2 equiv, 74.2 mmol) in one portion. The reaction was stirred and left at 0° C. for 1 h. Water (100 mL) was added to the reaction mixture and the contents poured into a separatory funnel. The organic layer was separated and washed with water (3×100 mL) and brine (100 mL). It was dried over anhydrous MgSO4, filtered, concentrated and dried under high vacuum to give a crude oil (6.23 g, 85.6%). This material was used without further purification. 1H NMR (CDCl3, 400 MHz): δ 1.47 (s, 6H), 1.82-1.90 (q, J=6.8, 2H), 1.92-2.00 (q, J=6.8, 2H), 2.45 (s, 2H), 3.44-3.50 (t, J=6.8, 4H). 1.43 (s, 6H), 2.11-2.15 (m, 2H), 3.09 (s, 3 H), 3.35 (s, 2H), 3.41 (dt, J=7.2, 4H). LRMS (ESI+) for C9H16N4O (196.1); Found: 197 (MH+).

Workup

  1. additionthe contents poured into a separatory funnel
  2. customThe organic layer was separated
  3. washwashed with water (3×100 mL) and brine (100 mL)
  4. dry with materialIt was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-edaf8cdca01a4b03918df421f2a40a4a
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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