tert-Butyl (2S)-2-(((4-methylbenzene-1-sulfonyl)oxy)methyl)pyrrolidine-1-carboxylate → HCID 59753061, compound

HRID 1909818Notes

Reaction equation

HRID 1909818 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC([N:27]1[CH2:31][CH2:30][CH2:29][C@H:28]1[CH2:32]OS(C1C=CC(C)=CC=1)(=O)=O)=O)(C)(C)C>>[CH2:1]([C:8]1[S:12][C:11]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:32][C@@H:28]3[CH2:29][CH2:30][CH2:31][NH:27]3)=[CH:17][CH:18]=2)=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 11783214tert-Butyl (2S)-2-(((4-methylbenzene-1-sulfonyl)oxy)methyl)pyrrolidine-1-carboxylateHCID 69000540HCID 69000540, compound

Product 1

HCID 59753061HCID 59753061, compoundYield 85%

Procedure

The title compound was prepared from the product of example 170, step 4 (0.3 g, 1.1 mmol) and (S)-2-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.5 g, 1.4 mmol) using the procedure of Example 159, step 5 with 85% yield (360 mg). 1HNMR (CD3OD) 7.50 (d, J=8.8 Hz, 2H), 7.39-7.18 (d, J=3.6 Hz, 5H), 7.08 (d, J=3.6 Hz, 1H), 7.00 (d, J=8.8 Hz, 1H), 6.77 (d, J=3.6 Hz, 1H), 4.58 (m, 1H), 4.32 (m, 1H), 4.12 (s, 2H), 4.03 (m, 2H), 3.34 (m, 2H), 2.26 (m, 1H), 2.10 (m, 2H), 1.90 (m, 1H), LC/MS (ESI+) m/z: 99%; 351 (M+1, 100). Elemental analysis

Sources & evidence

ORD record
ord-159d20ca3ea444a08afd969b9aa3dcb4
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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