Trifluoroacetic acid → (3R,5S)-5-(benzylamino-methyl)-1-methanesulfonyl-pyrrolidine-3-thiol trifluoro-acetate

HRID 1006784Notes

Reaction equation

[CH2:1]([NH:8][CH2:9][C@@H:10]1[CH2:14][C@@H:13]([S:15]CC2C=CC(OC)=CC=2)[CH2:12][N:11]1[S:25]([CH3:28])(=[O:27])=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37]>>[F:39][C:38]([F:41])([F:40])[C:36]([OH:42])=[O:37].[CH2:1]([NH:8][CH2:9][C@H:10]1[N:11]([S:25]([CH3:28])(=[O:27])=[O:26])[CH2:12][C@H:13]([SH:15])[CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 12052Triethylsilane

HCID 69430684(2S,4R)-benzyl-[1-methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidin-2-ylmethyl]-amine

Product 1

HCID 86584833(3R,5S)-5-(benzylamino-methyl)-1-methanesulfonyl-pyrrolidine-3-thiol trifluoro-acetateYield 91%

Conditions

Temperature: 80 °C

Procedure

(Method 2): 100 mg (0.24 mmol) of (2S,4R)-benzyl-[1-methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidin-2-ylmethyl]-amine was dissolved in 8.5 ml TFA and treated at 0° C. with 0.38 ml (2.38 mmol) triethylsilane. The reaction was warmed up over night, heated 1.5 h at 80° C. and evaporated, partitioned between water (10 ml)/Et2O (2×10 ml). The water was lyophilized to give 90 mg (91%) of (3R,5S)-5-(benzylamino-methyl)-1-methanesulfonyl-pyrrolidine-3-thiol trifluoro-acetate, MS: 301 (MH+).

Workup

temperatureThe reaction was warmed up over night
customevaporated
custompartitioned between water (10 ml)/Et2O (2×10 ml)

Sources & evidence

ORD record: ord-019c7e72e8a748aaae34742165627fe9
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06790860B2

Reaction notes

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