Acetyl chloride → trans-6-Acetylaminomethyl-3,4-dihydro-2,2-dimethyl-4-(2-oxopyrrolidinyl)-2H-1-benzopyran-3-ol

HRID 2166083Notes

Reaction equation

HRID 2166083 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[C@@H:9]([OH:14])[C@H:8]([N:15]3[CH2:19][CH2:18][CH2:17][C:16]3=[O:20])[C:7]=2[CH:21]=1.C(N(CC)CC)C.[C:29](Cl)(=[O:31])[CH3:30]>ClCCl>[C:29]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:12])([CH3:13])[C@@H:9]([OH:14])[C@H:8]([N:15]3[CH2:19][CH2:18][CH2:17][C:16]3=[O:20])[C:7]=2[CH:21]=1)(=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 6367Acetyl chloride2×HCID 8471TriethylamineHCID 67883096trans-6-Aminomethyl-3,4-dihydro-2,2-dimethyl-4-(2-oxopyrrolidinyl)-2H-1-benzopyran-3-ol

Product 1

HCID 67876043trans-6-Acetylaminomethyl-3,4-dihydro-2,2-dimethyl-4-(2-oxopyrrolidinyl)-2H-1-benzopyran-3-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the compound of example 10 (0.57 g) and triethylamine (0.55 ml) stirred in dichloromethane (50 ml) was added acetyl chloride (0.154 ml) dropwise, at 0° C. After 2 h at 0° C., more acetyl chloride (0.154 ml) was added and the reaction mixture stirred for a further 16 h and allowed to attain room temperature. The organic phase was washed with water and brine and dried over anhydrous magnesium sulphate. Filtration and evaporation gave the crude product (0.33 g) which was recrystallised from ethyl acetate-dichloromethane to give the title compound (0.24 g) as colourless crystals of mp 206°-208° C.

Workup

  1. customat 0° C
  2. customto attain room temperature
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationFiltration and evaporation
  6. customgave the crude product (0.33 g) which
  7. customwas recrystallised from ethyl acetate-dichloromethane

Sources & evidence

ORD record
ord-941b25962fcf491ab1d2495a86eab3d0
Source dataset
uspto-grants-1990_07
Patent number
US04943582

Reaction notes

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