Trichloroacetyl chloride → HCID 67618536, compound

HRID 2392832Notes

Reaction equation

HRID 2392832 reaction equation
[NH2:1][C@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([CH3:6])([OH:5])[CH3:4].[Cl:13][C:14]([Cl:19])([Cl:18])[C:15](Cl)=[O:16]>N1C=CC=CC=1>[OH:5][C:3]([CH3:6])([CH3:4])[C@H:2]([NH:1][C:15](=[O:16])[C:14]([Cl:19])([Cl:18])[Cl:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 6420Trichloroacetyl chlorideHCID 11240681(βR)-β-Amino-α,α-dimethylbenzeneethanol

Product 1

HCID 67618536HCID 67618536, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (13) (1.413 g, 8.56 mmol) in pyridine (24 ml) at 0° C. was added trichloroacetyl chloride (1.05 ml, 9.41 mmol). After stirring at this temperature for 10 minutes the reaction mixture was stirred overnight at room temperature. The reaction was quenched by the addition of saturated aqueous sodium chloride solution, after which the product was extracted with dichloromethane and the combined organic extracts were washed with hydrochloric acid (1M). Concentration in vacuo and purification by flash column chromatography using 30% ethyl acetate/40-60 petroleum ether as eluant furnished the title compound (14) (1.782 g, 65%) as a solid which was recrystallised from ether/40-60 petroleum ether; mp 97° C.; νmax (CHCl3) 1716 cm-1 ; [α]D24 (c 1 in CHCl3)=-55.5; (Found: C, 46.41; H, 4.26; N, 4.49. C12H14Cl3NO2 requires C, 46.40; H, 4.54; N, 4.51%); δH (200 MHz; CDCl3) 1.06 (3H, s, C(CH3)2), 1.39 (3H, s, C(CH3)2), 1.94 (1H, s, OH), 4.70 (1H, d, J=8.5, CHCH), 7.29-7.39 (5H, m, ArCH); δC (125 MHz; CDCl3) 27.70 (CH3), 27.86 (CH3), 63.06 (CH), 75.52 (C), 92.97 (CCl3), 128.13 (ArCH), 128.35 (ArCH), 128.71 (ArCH), 137.88 (C), 161.51 (CO); m/z (CI-, NH3) 310 (M+).

Workup

  1. stirringwas stirred overnight at room temperature
  2. customThe reaction was quenched by the addition of saturated aqueous sodium chloride solution
  3. extractionafter which the product was extracted with dichloromethane
  4. washthe combined organic extracts were washed with hydrochloric acid (1M)
  5. concentrationConcentration
  6. customin vacuo and purification by flash column chromatography

Sources & evidence

ORD record
ord-a7b428eb9e9a43fe8f5a5756a95d8622
Source dataset
uspto-grants-1998_09
Patent number
US05801249

Reaction notes

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