Acetyl chloride → (1R)-1,3,8,8-Tetramethyl-3-azabicyclo[3.2.1]octane-2,4-dione

HRID 1258119Notes

Reaction equation

HRID 1258119 reaction equation
[CH3:1][C@@:2]1([C:13]([OH:15])=O)[CH2:6][CH2:5][C@H:4]([C:7](=[O:10])[NH:8][CH3:9])[C:3]1([CH3:12])[CH3:11].C(Cl)(=O)C>C(OCC)(=O)C>[CH3:1][C@:2]12[C:3]([CH3:12])([CH3:11])[CH:4]([CH2:5][CH2:6]1)[C:7](=[O:10])[N:8]([CH3:9])[C:13]2=[O:15]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 42281543(1R,3S)-1,2,2-Trimethyl-3-(methylcarbamoyl)cyclopentanecarboxylic acid

Product 1

HCID 57518626(1R)-1,3,8,8-Tetramethyl-3-azabicyclo[3.2.1]octane-2,4-dione

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of step 1 intermediate (4.5 g, 21 mmol) in ethyl acetate, acetyl chloride (5.25 mL, 73 mmol) was added and refluxed for 24 hours. After the reaction, ethyl acetate was removed under reduced pressure, crude material purified by column, using ethyl acetate and hexane. (3.7 g) 1H NMR (400 MHz, CDCl3) δ ppm: 0.8 (s, 3H), 0.9 (s, 3H), 1.1 (s, 3H), 1.60-1.61 (m, 1H), 1.71-1.83 (m, 1H), 1.88-1.95 (m, 1H), 2.11-2.2 (m, 1H), 2.65 (d, 1H), 2.91 (s, 3H). m/z (M+H): 196.1.

Workup

  1. temperaturerefluxed for 24 hours
  2. customwas removed under reduced pressure, crude material
  3. custompurified by column

Sources & evidence

ORD record
ord-20a0f477a4bc4a3382e7460e83e4954e
Source dataset
uspto-grants-2013_06
Patent number
US08466145B2

Reaction notes

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