2,5-Difluorobenzaldehyde → HCID 69433288, compound

HRID 1006791Notes

Reaction equation

[C:1]([O:5][C:6]([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][N:34]=[N+]=[N-])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N1C[C@H](SC(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C[C@H]1CN)=O)(C)(C)C.[F:71][C:72]1[CH:79]=[CH:78][C:77]([F:80])=[CH:76][C:73]=1[CH:74]=O>>[C:1]([O:5][C:6]([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][NH:34][CH2:74][C:73]1[CH:76]=[C:77]([F:80])[CH:78]=[CH:79][C:72]=1[F:71])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 1376632,5-Difluorobenzaldehyde

HCID 11752390HCID 11752390, compound

HCID 69431247HCID 69431247, compound

Product 1

HCID 69433288HCID 69433288, compound

Procedure

From (2S,4R)-2-azidomethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester was prepared via (2S,4R)-2-aminomethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester [as light brown foam, MS: 475 (MH+)] and further reaction with 2,5-difluoro benzaldehyde analogously to reductive amination gave (2S,4R)-2-[(2,5-difluoro-benzylamino)-methyl]-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester as colorless oil MS: 601 (MH+) which was treated according to trityl cleavage (method 5) to give (2S,4R)-2-[(2,5-difluoro-benzylamino)-methyl]-4-mercapto-pyrrolidine-1-carboxylic acid tert-butyl ester as colorless liquid MS: 359 (MH+).

Sources & evidence

ORD record: ord-92fb198b04cc4f3e936636f06922f613
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06790860B2

Reaction notes

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