Bromomethylstyrene → (3R,5S)-1-methanesulfonyl-5-(3-phenyl-propoxymethyl)-pyrrolidine-3-thiol

HRID 1006812Notes

Reaction equation

[CH3:1][S:2]([N:5]1[CH2:9][C@H:8]([S:10]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:7][C@H:6]1[CH2:30][OH:31])(=[O:4])=[O:3].Br[CH2:33][CH:34]=[CH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>>[CH3:1][S:2]([N:5]1[C@H:6]([CH2:30][O:31][CH2:33][CH2:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:7][C@@H:8]([SH:10])[CH2:9]1)(=[O:3])=[O:4]

Participants

Reactant 3

HCID 98116Bromomethylstyrene

HCID 69433309(2S,4R)-(1-methanesulfonyl-4-tritylsulfanyl-pyrrolidin-2-yl)-methanol

HCID 131722655TFA triethylsilane

Product 1

HCID 86584849(3R,5S)-1-methanesulfonyl-5-(3-phenyl-propoxymethyl)-pyrrolidine-3-thiol

Procedure

(2S,4R)-(1-methanesulfonyl-4-tritylsulfanyl-pyrrolidin-2-yl)-methanol with 3-bromo-1-phenyl-1-propene, followed by hydrogenation (17 h) and TFA/triethylsilane deprotection (Method 3) gave (3R,5S)-1-methanesulfonyl-5-(3-phenyl-propoxymethyl)-pyrrolidine-3-thiol, MS: 329 (M).

Sources & evidence

ORD record: ord-ce10c176979244f68c8670fed21e6f73
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06790860B2

Reaction notes

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