Diisopropylethylamine → HCID 86754135, compound

HRID 1416785Notes

Reaction equation

HRID 1416785 reaction equation
Cl.[CH2:2]([O:4][C:5]([C:7]1([C:30]([O:32][CH2:33][CH3:34])=[O:31])[O:11][C:10]2[CH:12]=[CH:13][C:14]([CH2:16][C@H:17]([NH:19][CH2:20][C@@H:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)[OH:22])[CH3:18])=[CH:15][C:9]=2[O:8]1)=[O:6])[CH3:3].CCN(C(C)C)C(C)C.Cl[C:45]([O:47][CH2:48][C:49]([Cl:52])([Cl:51])[Cl:50])=[O:46]>C(Cl)Cl>[CH2:2]([O:4][C:5]([C:7]1([C:30]([O:32][CH2:33][CH3:34])=[O:31])[O:11][C:10]2[CH:12]=[CH:13][C:14]([CH2:16][C@H:17]([N:19]([CH2:20][C@@H:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)[OH:22])[C:45]([O:47][CH2:48][C:49]([Cl:52])([Cl:51])[Cl:50])=[O:46])[CH3:18])=[CH:15][C:9]=2[O:8]1)=[O:6])[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 870632,2,2-Trichloroethyl chloroformateHCID 86754136HCID 86754136, compound

Product 1

HCID 86754135HCID 86754135, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 3.0 g (5.83 mmol) (R,R)-5-{2-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester hydrochloride salt and 60 mL CH2Cl2 was added 2.54 mL (1.88 g, 14.57 mmol) of i-Pr2NEt followed by 0.84 mL (1.30 g, 6.12 mmol) of 2,2,2-trichloroethyl chloroformate. After stirring at room temperature for 6 h, the reaction mixture was quenched with 10 mL sat. aq. NaHCO3, and extracted with 3×100 mL Et2O. The combined organics were washed with 1×100 1N HCl, 1×100 mL brine, dried over MgSO4, filtered and evaporated to a yellow oil. Flash chromatography on silica gel, eluting with hexanes/EtOAc (4/1 to 2/1), gives 3.46 g (5.30 mmol, a 91% yield) of the title compound (Rf =0.32; 2/1 hexanes/EtOAc) as an oily, off-white solid; 1H NMR 300 MHz, CDCl3): δ 1.20-1.39 (complex m, 9H), 2.60-2.80 (m, 1H), 2.80-2.91 (m, 1H), 3.01-3.19 (m, 1H), 3.23-3.31 (m, 1H), 3.40-3.53 (m, 1H), 4.10-4.23 (m, 1H), 4.30-4.42 (complex m, 4H), 4.70-4.89 (m, 3H), 6.65-6.88 (complex m, 4H), 7.15-7.39 (complex m, 3H); MS (ES) m/z (relative intensity): 654 (M+ +H, 100).

Workup

  1. customthe reaction mixture was quenched with 10 mL sat. aq. NaHCO3
  2. extractionextracted with 3×100 mL Et2O
  3. washThe combined organics were washed with 1×100 1N HCl, 1×100 mL brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to a yellow oil
  7. washFlash chromatography on silica gel, eluting with hexanes/EtOAc (4/1 to 2/1)
  8. customgives 3.46 g (5.30 mmol

Sources & evidence

ORD record
ord-f7b7bed4b1c14c769331cab65f49e09f
Source dataset
uspto-grants-1999_06
Patent number
US05914339

Reaction notes

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