Benzyl Bromide → (2S,4R)-2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine

HRID 458348Notes

Reaction equation

HRID 458348 reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([S:13][C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[CH2:33][OH:34])=O)(C)(C)C.[CH2:35](Br)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[CH2:35]([O:34][CH2:33][C@@H:9]1[CH2:10][C@@H:11]([S:13][C:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:12][NH:8]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

3

Reactant 2

HCID 7498Benzyl BromideHCID 11271474(2S,4R)-2-hydroxymethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 69427603(2S,4R)-2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine

Procedure

In analogy: The reaction of (2S,4R)-2-hydroxymethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester with benzylbromide gave (2S,4R)-2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine, MS: 466 (MH+).

Sources & evidence

ORD record
ord-972c1392289a4c4b9d5920bea040dbe6
Source dataset
uspto-grants-2007_03
Patent number
US07189756B2

Reaction notes

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