Dimethyl Sulfoxide → (S)-2-Dibenzylamino-propionaldehyde
Reaction equation
C(Cl)(C(Cl)=O)=O.CS(C)=O.[CH2:11]([N:18]([C@@H:26]([CH3:29])[CH2:27][OH:28])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(CC)CC.[NH4+].[Cl-]>C(Cl)Cl>[CH2:19]([N:18]([C@@H:26]([CH3:29])[CH:27]=[O:28])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
To a cold (−78° C.) solution of (COCl)2 (2M in CH2Cl2, 2.47 mL, 4.94 mmol) in CH2Cl2 (8 mL), DMSO (0.70 mL, 9.89 mmol) was added dropwise. After stirring at −78° C. for 15 min, a solution of (S)-2-(N,N-dibenzylamino)-1-propanol (1.01 g, 3.96 mmol) in CH2Cl2 (10 mL) was added dropwise. The mixture was stirred at −78° C. for 1 h, and then Et3N (2.76 mL, 19.78 mmol) was added. The reaction was warmed up to 0° C. and stirred for 15 min, followed by the addition of NH4Cl (25 mL, sat. aq.). The crude was extracted with CH2Cl2 (3×25 mL), washed successively with NaHCO3 (50 mL, sat. aq.) and brine (50 mL), dried over Na2SO4 and concentrated in vacuo. Aldehyde 4 was obtained as a yellow oil and used without further purification (928 mg, 93% yield).
Workup
- stirringThe mixture was stirred at −78° C. for 1 h
- temperatureThe reaction was warmed up to 0° C.
- stirringstirred for 15 min
- extractionThe crude was extracted with CH2Cl2 (3×25 mL)
- washwashed successively with NaHCO3 (50 mL, sat. aq.) and brine (50 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-a4ad9b95332c4983b0ed449e679a4a72
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07138547B2
Reaction notes
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