Lithium diisopropylamide → 4-Tritylthiopyrrolidine

HRID 1755761Notes

Reaction equation

HRID 1755761 reaction equation
[Si](N1C(CO[Si](C(C)(C)C)(C)C)CCC1=O)(C(C)(C)C)(C)C.C([N-]C(C)C)(C)C.[Li+].C(OC([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]1CI)=O)C=C>>[C:43]([S:42][CH:40]1[CH2:41][NH:37][CH2:38][CH2:39]1)([C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1)([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

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 199344974-TritylthiopyrrolidineYield 32.9%

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-bb8dc13b8c3f4897a2f59593d661576b
Source dataset
uspto-grants-1995_08
Patent number
US05438054

Reaction notes

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