Water → tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate
Reaction equation
[H-].C([Al+]CC(C)C)C(C)C.CC[O:13][C:14]([C@@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=O.O>C1(C)C=CC=CC=1.C(OCC)C>[C:24]([O:23][C:21]([N:17]1[CH2:18][CH2:19][CH2:20][C@H:16]1[CH:14]=[O:13])=[O:22])([CH3:27])([CH3:25])[CH3:26]Participants
6
Conditions
- Temperature
- -78 °C
Procedure
At −78° C., a 1.2 M solution of diisobutylaluminum hydride (31.7 ml, 38 mmol) in toluene was added dropwise to a solution of (2S)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (4.02 g, 16.5 mmol) in diethyl ether (1.5 ml). The reaction mixture was stirred for 3 h at −78° C. Water (9.9 ml) was added dropwise. The reaction mixture was warmed to room temperature. The mixture was filtered through a plug of celite. The celite was washed with tert-butyl methyl ether (3×100 ml). The combined organic layers were dried over magnesium sulfate. The solvent was removed in vacuo, to give 2.34 g of crude N-t-butyloxycarbonyl-(S)-prolinal, which was used for the next step without further purification.
Workup
- temperatureThe reaction mixture was warmed to room temperature
- filtrationThe mixture was filtered through a plug of celite
- washThe celite was washed with tert-butyl methyl ether (3×100 ml)
- dry with materialThe combined organic layers were dried over magnesium sulfate
- customThe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-6a4543f47ca04c0c81c04623c40bb4f1
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06919315B1
Reaction notes
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