Lithium diisopropylamide → (2R,4S)-N-allyloxycarbonyl-2-(2-oxoazetidin-3-ylmethyl)-4-tritylthiopyrrolidine

HRID 1755760Notes

Reaction equation

HRID 1755760 reaction equation
[Si]([N:8]1[CH2:11][CH2:10][C:9]1=[O:12])(C(C)(C)C)(C)C.C([N-]C(C)C)(C)C.[Li+].[CH2:21]([O:24][C:25]([N:27]1[CH2:31][C@@H:30]([S:32][C:33]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:29][C@H:28]1[CH2:52]I)=[O:26])[CH:22]=[CH2:23]>>[CH2:21]([O:24][C:25]([N:27]1[CH2:31][C@@H:30]([S:32][C:33]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:29][C@H:28]1[CH2:52][CH:10]1[CH2:11][NH:8][C:9]1=[O:12])=[O:26])[CH:22]=[CH2:23]

Participants

4

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 140681681-(tert-Butyldimethylsilyl)azetidin-2-oneHCID 57112975(2S,4S)-N-allyloxycarbonyl-2-iodomethyl-4-tritylthiopyrrolidine

Product 1

HCID 56992111(2R,4S)-N-allyloxycarbonyl-2-(2-oxoazetidin-3-ylmethyl)-4-tritylthiopyrrolidineYield 24.5%

Procedure

The same procedure as in Reference Example 22-1 was carried out by using N-tert-butyldimethylsilyl-2-oxoazetidine (650 mg, 3.5 mmol), lithium diisopropylamide (2.1M tetrahydrofuran solution, 3.34 ml, 7.0 mmol), and (2S,4S)-N-allyloxycarbonyl-2-iodomethyl-4-tritylthiopyrrolidine (1 g, 1.75 mmol) to obtain (2R,4S)-N-allyloxycarbonyl-2-(2-oxoazetidin-3-ylmethyl)-4-tritylthiopyrrolidine (220 mg, yield: 24%).

Sources & evidence

ORD record
ord-79f7542364294db393603928ce004a30
Source dataset
uspto-grants-1995_08
Patent number
US05438054

Reaction notes

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