Propanal → 4-But-3-enyl-5-ethyl-2,2-diphenyl-oxazolidine-4-carboxylic acid tert-butyl ester

HRID 579522Notes

Reaction equation

HRID 579522 reaction equation
[C:1]([O:5][C:6](=[O:26])[CH:7]([N:12]=[C:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:8][CH2:9][CH:10]=[CH2:11])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl-].C([Al+]CC)C.[CH:43](=[O:46])[CH2:44][CH3:45]>C1COCC1>[C:1]([O:5][C:6]([C:7]1([CH2:8][CH2:9][CH:10]=[CH2:11])[CH:43]([CH2:44][CH3:45])[O:46][C:13]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:12]1)=[O:26])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 527PropanalHCID 2724254Sodium bis(trimethylsilyl)amideHCID 160669741,1-Dimethylethyl 2-[(diphenylmethylene)amino]-5-hexenoateHCID 16686102Diethyl aluminum chloride

Product 1

HCID 668332184-But-3-enyl-5-ethyl-2,2-diphenyl-oxazolidine-4-carboxylic acid tert-butyl esterYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

While under a nitrogen atmosphere, a stirred solution of 2-(benzhydrylidene-amino)-hex-5-enoic acid tert-butyl ester (350 mg, 1 mmol) in THF (5 mL, 0.2 M) was cooled to −78° C. and carefully treated with sodium bis(trimethylsilyl)amide (2 mL, 1 M, 2 equiv). After stirring 30 min, diethyl aluminum chloride (2.4 mL, 1 M, 2.4 equiv) was added and the reaction mixture was stirred an additional 30 min. Propionaldehyde (94 μl, 1.25 mmol, 1.25 eq) was added to the solution and the cooling bath was removed. After stirring overnight the reaction mixture was cooled to 0° C. and quenched with saturated NH4Cl. The resulting solution was diluted with ethyl acetate and washed successively with water and saturated potassium sodium tartrate, dried over MgSO4, filtered and concentrated. Purification by MPLC (1-40% ethyl acetate in heptane) gave 4-but-3-enyl-5-ethyl-2,2-diphenyl-oxazolidine-4-carboxylic acid tert-butyl ester (349 mg, 0.86 mmol, 86%).

Workup

  1. stirringthe reaction mixture was stirred an additional 30 min
  2. customthe cooling bath was removed
  3. stirringAfter stirring overnight the reaction mixture
  4. customquenched with saturated NH4Cl
  5. additionThe resulting solution was diluted with ethyl acetate
  6. washwashed successively with water and saturated potassium sodium tartrate
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by MPLC (1-40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-c5ae4b94a0f84a3eb884600a758f3701
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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