(R)-tert-Butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate → HCID 59753016, compound

HRID 1909808Notes

Reaction equation

HRID 1909808 reaction equation
[C:1]1([C:7]2[O:11][C:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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>>[C:1]1([C:7]2[O:11][C:10]([CH2:12][C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:32][C@H:28]4[CH2:29][CH2:30][CH2:31][NH:27]4)=[CH:17][CH:18]=3)=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 11760051(R)-tert-Butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylateHCID 69004834HCID 69004834, compound

Product 1

HCID 59753016HCID 59753016, compoundYield 60%

Procedure

The title compound (80 mg, 50%) was prepared from the product of step 4 (0.1 g, 0.4 mmol) and (R)-2-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.17 g, 0.48 mmol) using the procedure of Example 154, step 3; 1HNMR (400 MHz, CD3OD) δ 7.58 (d, J=8 Hz, 2H), 7.32 (t, J=6 Hz, 2H), 7.26 (d, J=8 Hz, 2H), 7.19 (t, J=8 Hz, 1H), 7.17 (d, J=3.6 Hz, 1H), 6.98 (d, J=8.4 Hz, 2H), 6.63 (d, J=3.2 Hz, 1H), 6.09 (d, J=3.2 Hz, 1H), 4.32 (dd, J=7.2, 3.6 Hz, 1H), 4.08 (t, J=9.4 Hz, 1H), 4.01 (m, 1H), 3.98 (s, 2H), 3.35 (m, 2H), 2.25 (m, 1H), 2.11 (m, 2H), 1.98 (m, 1H); LC/MS (ESI+) m/z: 91%; 334 (M+1, 100).

Sources & evidence

ORD record
ord-29b083ee63ec4ccfab49f4a64a9727ee
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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