Dimethyl Sulfoxide → (S)-2,2-Dimethyl-3-(1-oxoheptyl)-4-oxazolidinecarboxaldehyde
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]1([CH3:27])[N:16]([C:17](=[O:24])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C@H:15]([CH2:25][OH:26])[CH2:14][O:13]1.C(N(CC)CC)C>C(Cl)Cl.O>[CH3:27][C:12]1([CH3:11])[N:16]([C:17](=[O:24])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C@H:15]([CH:25]=[O:26])[CH2:14][O:13]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -60 °C
Procedure
A solution of oxalyl chloride (105 μl, 1.23 mmol) in CH2Cl2 (2.75 mL) is cooled to -60° C. A solution of DMSO (192 μL) in CH2Cl2 (0.55 mL) is added over a period of 5 min. and the resulting milky mixture is stirred for 15 min at -60° C. The alcohol from Example 39 (133 mg., 0.55 mmol) in CH2Cl2 (0.55 ml) is added to the mixture over 5 min. The bath is allowed to warm up to -20° C. (20 min.) and the clear solution is stirred for 20 min. at -20° C. Triethylamine (0.77 mL) and H2O (3.4 mL) are added and the mixture is stirred for 5 minutes at ambient temperature. Workup with CH2Cl2 gives a crude oil which is purified by chromatography (1.5×20 cm, 3:1 together) to give 9a: NMR δ 0.85 (m, 3H), 1.30 (m, 6H), 1.60 (s, 3H), 1.60-1.70 (m, 2H), 1.70 (s, 3H), 2.00-2.40 (m, 2H), 4.00-4.30 (m, 3H), 9.65 (d, J≃1,1H).
Workup
- temperatureto warm up to -20° C. (20 min.)
- stirringthe clear solution is stirred for 20 min. at -20° C
- stirringthe mixture is stirred for 5 minutes at ambient temperature
- customis purified by chromatography (1.5×20 cm, 3:1 together)
Sources & evidence
- ORD record
- ord-81c6b6aa91364219840f78d0eb0d5116
- Source dataset
- uspto-grants-1997_08
- Patent number
- US05658945
Reaction notes
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