Acetyl chloride → HCID 178474956, compound

HRID 585648Notes

Reaction equation

HRID 585648 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH:12]=[CH:11][C:10]=1[C@@H:23]1[CH2:28][CH2:27][C@H:26]([NH2:29])[CH2:25][CH2:24]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:30](Cl)(=[O:32])[CH3:31]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[Si:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][Si:16]([C:19]([CH3:20])([CH3:21])[CH3:22])([CH3:18])[CH3:17])[CH:12]=[CH:11][C:10]=1[C@@H:23]1[CH2:24][CH2:25][C@H:26]([NH:29][C:30](=[O:32])[CH3:31])[CH2:27][CH2:28]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 178455051HCID 178455051, compound

Product 1

HCID 178474956HCID 178474956, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

trans/cis-4-(2,4-Bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexylamine (27 mg) was dissolved in pyridine (0.5 ml). Acetyl chloride (6 μl) and 4-dimethylaminopyridine (2 mg) were added sequentially and the reaction mixture stirred for 24 hr. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (10 ml) and water (2 ml). The aqueous phase was extracted with ethyl acetate (2×5 ml) and the combined organic phases were washed with brine (10 ml), dried over anhydrous magnesium sulphate, and concentrated to give a brown oil. Purification via flash column chromatography (SiO2 eluting with ethyl acetate:petroleum ether, 7:3 v/v) afforded the title product as a white solid (15 mg, 50%) and a mixture of diastereoisomers. δH (CDCl3): 0.17 (3H, s), 0.19 (3H, s), 0.21 (3H, s), 0.22 (3H, s), 0.96 (9H, s), 1.02 (9H, s), 1.06-1.20 (2H, m), 1.36-1.54 (2H, m), 1.60-1.75 (2H, m), 1.80-1.92 (2H, m), 1.95 (1.5H, s), 2.00 (1.5H, s), 2.75-2.90 (1H, m), 3.76-3.87 (1H, m), 5.34-5.39 (0.5H, d), 5.72-5.77 (0.5H, d), 6.26-6.29 (1H, m), 6.38-6.41 (1H, m), 6.93 (0.5H, d), 6.95 (0.5H, d); m/z (ES+) 478 (M+1)+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate (10 ml) and water (2 ml)
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×5 ml)
  4. washthe combined organic phases were washed with brine (10 ml)
  5. dry with materialdried over anhydrous magnesium sulphate
  6. concentrationconcentrated
  7. customto give a brown oil
  8. customPurification via flash column chromatography (SiO2 eluting with ethyl acetate:petroleum ether, 7:3 v/v)

Sources & evidence

ORD record
ord-6bad569b96a249c082b86f9e9eb6a3a0
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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