Acetyl chloride → HCID 86656058, compound

HRID 1260478Notes

Reaction equation

HRID 1260478 reaction equation
[C:1]1([CH:7]2[CH2:11][NH:10][CH2:9][CH:8]2[NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20](Cl)(=[O:22])[CH3:21].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:20]([N:10]1[CH2:11][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])[CH2:9]1)(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 3856984HCID 3856984, compound

Product 1

HCID 86656058HCID 86656058, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice cooled stirred solution of tert-butyl (4-phenylpyrrolidin-3-yl)carbamate (prepared as described in J. Med. Chem. 1993, 36, 4139 starting from (2E)-3-phenylprop-2-enoic acid) (1.0 eq.) in dry DCM (0.1M) were slowly added acetyl chloride (4.0 eq.) and DIPEA (4.0 eq.). The reaction mixture was stirred for 1 h at RT, then diluted with DCM, washed with sat. aq. NaHCO3 sol., water and brine. The solution was dried (Na2SO4), filtered and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography eluting with 5-100% EtOAc/petroleum ether, then eluting with 0-10% MeOH/EtOAc affording the titled compound as yellow oil. MS (ES) C17H24N2O3 requires: 304, found: 305 (M+H)+.

Workup

  1. washwashed with sat. aq. NaHCO3 sol., water and brine
  2. dry with materialThe solution was dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customThe crude product was purified by flash chromatography
  6. washeluting with 5-100% EtOAc/petroleum ether
  7. washeluting with 0-10% MeOH/EtOAc affording the titled compound as yellow oil

Sources & evidence

ORD record
ord-8b632069e20841d3b1cb7af13939bcc9
Source dataset
uspto-grants-2013_06
Patent number
US08470823B2

Reaction notes

Loading…