(S)-tert-Butyl 4-oxo-2-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidine-1-carboxylate → (S)-tert-Butyl 2-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-4-(((trifluoromethyl)sulfonyl)oxy)-2,5-dihydro-1H-pyrrole-1-carboxylate

HRID 339261Notes

Reaction equation

HRID 339261 reaction equation
[C@H:1]1([NH:11][C:12]([C@@H:14]2[CH:18]=[C:17]([O:19][S:20]([C:23]([F:26])([F:25])[F:24])(=[O:22])=[O:21])[CH2:16][N:15]2[C:27]([O:29]CC2C=CC=CC=2)=[O:28])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.O=C1CN(C(O[C:46]([CH3:49])([CH3:48])[CH3:47])=O)[C@H](C(=O)N[C@H]2C3C(=CC=CC=3)CCC2)C1>>[C@H:1]1([NH:11][C:12]([C@@H:14]2[CH:18]=[C:17]([O:19][S:20]([C:23]([F:26])([F:24])[F:25])(=[O:22])=[O:21])[CH2:16][N:15]2[C:27]([O:29][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:28])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 86705874(S)-tert-Butyl 4-oxo-2-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidine-1-carboxylateHCID 86705883(S)-benzyl 2-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-4-(((trifluoromethyl)sulfonyl)oxy)-2,5-dihydro-1H-pyrrole-1-carboxylate

Product 1

HCID 86705901(S)-tert-Butyl 2-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-4-(((trifluoromethyl)sulfonyl)oxy)-2,5-dihydro-1H-pyrrole-1-carboxylateYield 61%

Procedure

Following a procedure analogous to that for the synthesis of Compound B of Example 22, (S)-tert-butyl 4-oxo-2-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidine-1-carboxylate (3.38 g, 9.43 mmol) was converted to the title compound (2.82 g, 61%). MS (ESI+) m/z 491.2 (M+H)+.

Sources & evidence

ORD record
ord-d4822c3493f44f89b639a228d6927aac
Source dataset
uspto-grants-2014_11
Patent number
US08889712B2

Reaction notes

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