Bromide ion → HCID 58171626, compound
Reaction equation
CON(C)[C:4]([CH:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]1)=[O:5].[Br-].[CH2:20]1[CH2:24]OC[CH2:21]1>>[C:4]([CH:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:7]1)(=[O:5])[C:21]#[C:20][CH3:24]Participants
4
Conditions
- Temperature
- -78 °C
Procedure
To a stirred mixture of tert-butyl 3-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate (2 g, 7.75 mmol) in dry THF (10 mL) was added 1-propynylmagnesinm bromide (30 mL, 15 mmol) under N2 at −78° C. The reaction mixture was stirred at −78° C. for 0.5 h, allowed to warm to rt slowly and stirred for another 10 h. The mixture was quenched with 2 N aq HCl (20 mL) at 0° C. and extracted with EtOAc (50 mL×3). The combined organic layers were washed with water (20 mL) and brine (20 mL), dried over Na2SO4 and concentrated. The residue was purified by preparative TLC (PE/EA=1:1) to afford tert-butyl 3-(but-2-ynoyl)pyrrolidine-1-carboxylate (1.6 g, 86%) as a white oil.
Workup
- temperatureto warm to rt slowly
- stirringstirred for another 10 h
- customThe mixture was quenched with 2 N aq HCl (20 mL) at 0° C.
- extractionextracted with EtOAc (50 mL×3)
- washThe combined organic layers were washed with water (20 mL) and brine (20 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customThe residue was purified by preparative TLC (PE/EA=1:1)
Sources & evidence
- ORD record
- ord-2b437fec08bc4f898af1bcce28bea8e2
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09163012B2
Reaction notes
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