Triethylamine → tert-Butyl 1-((2R,5S)-2,5-Dimethylpyrrolidine-1-carbonyl)cyclopentylcarbamate
Reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:14]([OH:16])=O)[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:17](N(CC)CC)C.CN(C(ON1N=N[C:34]2[CH:35]=[CH:36][CH:37]=[N:38][C:33]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:17][C@@H:37]1[CH2:36][CH2:35][C@H:33]([CH3:34])[N:38]1[C:14]([C:9]1([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:10][CH2:11][CH2:12][CH2:13]1)=[O:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
To a suspension of 1-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid (500 mg, 2.181 mmol), (2R,5S)-2,5-dimethylpyrrolidine, HCl (296 mg, 2.181 mmol), and triethylamine (0.912 mL, 6.54 mmol) in DMF (5 mL) was added HATU (829 mg, 2.181 mmol). The mixture was stirred at 23° C. for 4 h then concentrated. The residue was taken up in EtOAc (25 mL) then washed successively with 0.5 M HCl (2×25 mL), saturated NaHCO3 (2×25 mL), and brine (2×25 mL). The combined organic layers were dried (MgSO4), filtered, then concentrated under reduced pressure. The residue was purified by silica gel flash chromatography to give the title compound (0.47 g) as a white solid. LCMS m/z=311.3 [M+H]+.
Workup
- concentrationthen concentrated
- washthen washed successively with 0.5 M HCl (2×25 mL), saturated NaHCO3 (2×25 mL), and brine (2×25 mL)
- dry with materialThe combined organic layers were dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel flash chromatography
Sources & evidence
- ORD record
- ord-69c00f963c234f92aadbdf892edab5fc
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778950B2
Reaction notes
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