Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | N,N-Dimethylethylenediamine | HCID 66053 | — |
| Reactant | Benzyl 3-(chlorosulfonyl)pyrrolidine-1-carboxylate | HCID 53229936 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 66698088 | HCID 66698088 | 88% |
Reaction Steps
A solution of 3-chlorosulfonyl-pyrrolidine-1-carboxylic acid benzyl ester (110 mg, 0.362 mmol) in CH2Cl2 (1.5 mL) was added to a solution of N,N-dimethylethylenediamine (0.20 mL, 1.83 mmol) in CH2Cl2 (1 mL) at 0° C. The mixture was stirred at 0° C. for 10 min, and then warmed to room temperature and stirred for 1 hr. Water was added and the phases were separated. The aqueous phase was extracted with CH2Cl2 (2×), the combined organic extracts were dried (Na2SO4), and the solvent was removed under vacuum to give benzyl 3-({[2-(dimethylamino)ethyl]amino}sulfonyl)-1-pyrrolidinecarboxylate (102 mg, 88%), which was used in the next step without further purification: 1H NMR (CDCl3) δ 7.36-7.29 (m, 5H), 5.14 (d, J=1.8 Hz, 2H), 3.80-3.72 (m, 4H), 3.50 (m, 1H), 3.16 (br s, 2H), 2.42 (t, J=5.7 Hz, 2H), 2.31 (m, 2H), 2.21 (s, 6H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08461158B2 |
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| Source dataset | uspto-grants-2013_06 |
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| ORD ID | ord-ce4855655f6f4b2386c7ef8dee07e178 |
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| Source note | uspto-grants-2013_06 |
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