proline dl-form → 1-(4-Fluoro-benzenesulfonyl)-pyrrolidine-2-carboxylic acid isopropyl ester

HRID 351682Notes

Reaction equation

[NH:1]1[CH2:8][CH2:7][CH2:6][CH:2]1[C:3]([OH:5])=[O:4].[F:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.[CH:20](O)([CH3:22])[CH3:21]>>[CH:20]([O:4][C:3]([CH:2]1[CH2:6][CH2:7][CH2:8][N:1]1[S:16]([C:13]1[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=1)(=[O:18])=[O:17])=[O:5])([CH3:22])[CH3:21]

Participants

Reactant 3

HCID 614proline dl-form

HCID 3776Isopropanol

HCID 95884-Fluorobenzenesulfonyl chloride

Product 1

HCID 699004021-(4-Fluoro-benzenesulfonyl)-pyrrolidine-2-carboxylic acid isopropyl ester

Procedure

The title compound was prepared from DL-proline, isopropanol, and 4-fluorobezenesulfonyl chloride according to the procedure of Intermediate 48 as a clear oil; 1H NMR (CDCl3) δ 1.21-1.28 (m, 6H), 1.80-1.85 (m, 1H), 1.95-2.10 (m, 3H), 3.31-3.49 (m, 2H), 4.26-4.36 (m, 1H), 4.95-5.08 (m, 1H), 7.15-7.23 (m, 2H), 7.89-8.08 (m, 2H); MS (ES) m/z 315.8 (MH+); HRMS for C14H18FNO4S: 338.0830 (M+Na)

Sources & evidence

ORD record: ord-8c0c9a7eeb6e4a0eb32bd5e8f807e9a8
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743787B2

Reaction notes

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