Lithium diisopropylamide → (2R,4S)-N-allyloxycarbonyl-2-[(5S)-5-hydroxymethyl-2-oxopyrrolidin-3-ylmethyl]-4-tritylthiopyrrolidine

HRID 1492818Notes

Reaction equation

HRID 1492818 reaction equation
[Si]([N:8]1[CH:12]([CH2:13][O:14][Si](C(C)(C)C)(C)C)[CH2:11][CH2:10][C:9]1=[O:22])(C(C)(C)C)(C)C.C([N-]C(C)C)(C)C.[Li+].[CH2:31]([O:34][C:35]([N:37]1[CH2:41][C@@H:40]([S:42][C:43]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:39][C@H:38]1[CH2:62]I)=[O:36])[CH:32]=[CH2:33]>>[CH2:31]([O:34][C:35]([N:37]1[CH2:41][C@@H:40]([S:42][C:43]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:39][C@H:38]1[CH2:62][CH:10]1[CH2:11][C@@H:12]([CH2:13][OH:14])[NH:8][C:9]1=[O:22])=[O:36])[CH:32]=[CH2:33]

Participants

4

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 57036326N-tert-butyldimethylsilyl-5-tert-butyldimethylsiloxymethyl-2-oxopyrrolidineHCID 57112975(2S,4S)-N-allyloxycarbonyl-2-iodomethyl-4-tritylthiopyrrolidine

Product 1

HCID 57189868(2R,4S)-N-allyloxycarbonyl-2-[(5S)-5-hydroxymethyl-2-oxopyrrolidin-3-ylmethyl]-4-tritylthiopyrrolidineYield 21%

Procedure

The same procedure as in Reference Example 22-1 was carried out by using N-tert-butyldimethylsilyl-5-tert-butyldimethylsiloxymethyl-2-oxopyrrolidine (10.67 g, 31.6 mmol), lithium diisopropylamide (2.1M tetrahydrofuran solution, 15.1 ml, 31.6 mmol) and (2S,4S)-N-allyloxycarbonyl-2-iodomethyl-4-tritylthiopyrrolidine (10 g, 17.6 mmol) to obtain (2R,4S)-N-allyloxycarbonyl-2-[(5S)-5-hydroxymethyl-2-oxopyrrolidin-3-ylmethyl]-4-tritylthiopyrrolidine (2 g, yield: 21%).

Sources & evidence

ORD record
ord-ff67efe4b82f4f33816effd65cff8a64
Source dataset
uspto-grants-1994_12
Patent number
US05374720

Reaction notes

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