Toluene → HCID 89996173, compound
Reaction equation
C([C:3]1([C:22]([O-])=[O:23])[NH:8][C:7]2[CH2:9][O:10][C:11]3([CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12]3)[C:6]=2[CH:5]=[CH:4]1)C.CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1>C(Cl)Cl>[CH:22]([C:3]1[N:8]=[C:7]2[CH2:9][O:10][C:11]3([CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12]3)[C:6]2=[CH:5][CH:4]=1)=[O:23]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To the stirred solution of 1-tert-butyl 2′-ethyl-7′H-spiro[azetidine-3,5′-furo[3,4-b]pyridine]-1,2′-dicarboxylate (0.5 g, 1.5 mmol, 1 eq.) in DCM (18 mL) at −78° C. under nitrogen atmosphere was added 25% DIBAL-H in toluene (0.64 g, 2.6 mL, 4.5 mmol, 3 eq.). Resulting reaction mixture was stirred at −78° C. for 1 hour under nitrogen atmosphere. After complete consumption of starting material, reaction mixture was quenched by methanol (1.5 mL) followed by addition of saturated solution of sodium potassium tartarate salt (10 mL) at −78° C. and extracted with DCM (3×75 mL). Combined organic layer was dried over sodium sulphate, concentrated under reduced pressure to afford the title compound as brown solid (0.25 g, crude). Crude compound was used as such for the next reaction. LC-MS (m/z): 291.0 (M+H).
Workup
- customResulting
- customreaction mixture
- customAfter complete consumption of starting material, reaction mixture
- customwas quenched by methanol (1.5 mL)
- additionfollowed by addition of saturated solution of sodium potassium tartarate salt (10 mL) at −78° C.
- extractionextracted with DCM (3×75 mL)
- dry with materialCombined organic layer was dried over sodium sulphate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-16d5bfb8848b43218a1fc02e8f4db262
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09131697B2
Reaction notes
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