Tetrahydrofuran → HCID 67517692, compound
Reaction equation
[O:1]=[C:2]1[CH2:7][N:6]([C:8]([O:10][CH2:11][CH:12]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=3)=[O:9])[CH2:5][CH2:4][N:3]1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].C1COCC1.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[OH:1][CH:2]1[CH2:7][N:6]([C:8]([O:10][CH2:11][CH:12]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:19]3[C:24]2=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:9])[CH2:5][CH2:4][N:3]1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]Participants
Conditions
- Temperature
- -78 °C
Procedure
In a pre-dried RB flask, 1-tert-butyl 4-(9H-fluoren-9-ylmethyl) 2-oxopiperazine-1,4-dicarboxylate (6.5 g, 15.39 mmol) was dissolved in CH2Cl2 (150 mL) and THF (15 mL) under N2 and was cooled down to −78° C. DIBAL-H (23.08 mL, 23.08 mmol) was added slowly. Let reaction stir at −78° C. for 2 hours. Then saturated Rochelle's salt water solution (150 mL) was added to quenched reaction. Reaction was slowly warmed up to room temperature. Then it was passed through a Celite® pad. Filtering pad was washed with ether (100 mL×2). Then layers were separated and aq. layer was extracted with 50 mL of EtOAc twice. Organic phases were combined and were washed with water and brine (50 mL) respectively. Then it was passed anhydrous Na2SO4. Concentration gave crude product as white solid that was used directly in next step. LC/MS: (M+23)+=447.16
Workup
- customreaction
- customto quenched
- customreaction
- customReaction
- temperaturewas slowly warmed up to room temperature
- filtrationFiltering pad
- washwas washed with ether (100 mL×2)
- customThen layers were separated
- extractionaq. layer was extracted with 50 mL of EtOAc twice
- washwere washed with water and brine (50 mL) respectively
- concentrationConcentration
- customgave crude product as white solid that
Sources & evidence
- ORD record
- ord-0133e27cb6cd49ef8490600b0e3f9046
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09056859B2
Reaction notes
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