(2S,4S)-1-tert-butyl 2-methyl 4-chloropyrrolidine-1,2-dicarboxylate → HCID 86585076, compound
Reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13]([C@@H:15]1[CH2:19][C@H:18]([Cl:20])[CH2:17][N:16]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=O>C1COCC1>[C:24]([O:23][C:21]([N:16]1[CH2:17][C@@H:18]([Cl:20])[CH2:19][C@H:15]1[CH:13]=[O:12])=[O:22])([CH3:27])([CH3:26])[CH3:25]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
57 ml (57 mmol, 1.2 M soltion in toluene) of diisobutylaluminium hydride (DIBAH) was added during 40 min to a cold solution (-78° C.) of 6 g (22.7 mmol) (2S,4S)-4-Chloro-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester in 180 ml THF. The reaction was stirred for 2 h at −78° C. and quenched with a suspension of 23 g silica gel/23 g MgSO4.7H2O in 70 ml aqueous 10% KHSO4. The suspension was stirred for 15 min at room temperature, filtered and washed with THF. After evaporation of the THF, the residue was taken up in CH2Cl2, dried over Na2SO4 and evaporated to give 5.88 g crude (2S,4S)-4-Chloro-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester. Preparation of ketones and alcohols:
Workup
- customquenched with a suspension of 23 g silica gel/23 g MgSO4.7H2O in 70 ml aqueous 10% KHSO4
- stirringThe suspension was stirred for 15 min at room temperature
- filtrationfiltered
- washwashed with THF
- customAfter evaporation of the THF
- dry with materialdried over Na2SO4
- customevaporated
Sources & evidence
- ORD record
- ord-87cfd48c9f8c4b988073bccc4f436285
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06541638B2
Reaction notes
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