HCID 22609181, compound → HCID 25023068, compound

HRID 1367608Notes

Reaction equation

HRID 1367608 reaction equation
CC(C)([O-:4])C.[K+].C[C:8]1([CH3:16])[N:12]([CH2:13][CH2:14][OH:15])[CH2:11][CH2:10][O:9]1.[CH2:17]([CH:20]([CH2:27][CH2:28][CH3:29])[CH2:21][CH2:22][CH2:23]C1CO1)[CH2:18][CH3:19]>C(OCC)C>[OH:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10][O:9][CH2:8][CH:16]([OH:4])[CH2:19][CH2:18][CH2:17][CH:20]([CH2:21][CH2:22][CH3:23])[CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 22609181HCID 22609181, compoundHCID 23665647Potassium tert-butoxideHCID 24742642HCID 24742642, compound

Product 1

HCID 25023068HCID 25023068, compoundYield 177.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
75 °C

Procedure

To a 10 mL Schlenk tube containing potassium tert-butoxide (125 mg, 1 mmol, 0.5 eq.) under nitrogen atmosphere, was added freshly distilled 2,2-dimethyl-3-(2-hydroxyethyl)-oxazolidine (1.4 mL, 10 mmol, d 1.035, 5 eq.) before heating at 75° C. until complete dissolution. To the solution was added slowly 2-(4-propyl-heptyl)-oxirane (0.43 mL, 2 mmol, d 0.856) over 1 h at 75° C. The reaction was stirred at 75° C. After 6 h, the reaction was cooled to room temperature before adding diethyl ether (40 mL). The organic phase was extracted with aqueous hydrochloric acid (1M, 3×12 mL). Then, a solution of aqueous sodium hydroxide (25%) was added to bring the mixture to pH 14 before extracting it with diethyl ether (4×16 mL). The combined organic phases were dried over sodium sulfate and concentrated to afford the title compound (515 mg, 90% yield). 1H NMR (CDCl3, 400 MHz) d?(ppm): 3.83-3.74 (m, H); 3.67 (t, J=5.2 Hz, 2H); 3.67-3.56 (m, 2H); 3.52 (dd, J=2.7 Hz, J=9.9 Hz, H); 3.30 (dd, J=8.2 Hz, J=9.9 Hz, H); 3.05-2.96 (m, 2H+2H); 1.50-1.15 (m, 15H); 0.87 (t, J=7.0 Hz, 6H). 13C NMR (CDCl3, 129.9 MHz) d?(ppm): 75.9; 70.3; 70.2; 60.9; 51.1; 48.9; 36.9; 36.0 (2C); 33.7; 33.6; 22.7; 19.8 (2C); 14.5 (2C).

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. extractionThe organic phase was extracted with aqueous hydrochloric acid (1M, 3×12 mL)
  3. additionThen, a solution of aqueous sodium hydroxide (25%) was added
  4. extractionbefore extracting it with diethyl ether (4×16 mL)
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-754526513a454914a86e8ecc040a7679
Source dataset
uspto-grants-2011_02
Patent number
US07893258B2

Reaction notes

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