Ethyl Acetate → HCID 178514592, compound

HRID 397170Notes

Reaction equation

HRID 397170 reaction equation
Cl[CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C@H:8]1[CH2:13][CH2:12][C@@H:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1.[N-:22]=[N+:23]=[N-:24].[Na+].C(OCC)(=O)C>CS(C)=O>[N:22]([CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C@H:8]1[CH2:13][CH2:12][C@@H:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[N+:23]=[N-:24]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 178505694HCID 178505694, compound

Product 1

HCID 178514592HCID 178514592, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirring solution of (2S)-2-(chloromethyl)-1-[cis-4-(4-fluorobenzyl)cyclohexyl]pyrrolidine in 2 ml of DMSO (Aldrich) at 25° C. under N2 was added sodium azide (28 mg, 2.90 mmol, Aldrich). The reaction was heated at 50° C. for 16 hours. Worked up by adding ethyl acetate then rinsing 5 times with H2O. The organic was dried over magnesium sulfate, and concentrated in vacuo to obtain 45 mg of an amber oil as product. MS (ESI) detects 317 (M+H).

Workup

  1. washthen rinsing 5 times with H2O
  2. dry with materialThe organic was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-700425b4c6fa4375bbfbb554ae3b6b6a
Source dataset
uspto-grants-2003_08
Patent number
US06608227B1

Reaction notes

Loading…