(2R,3R)-3-(tert-Butyl-dimethylsilanyloxy)-2-[(1R)-(2,2,2-trifluoro-1-hydroxyethyl)]pyrrolidine-1-carboxylic acid tert-butyl ester → (1S,7R,7aR)-2-Chloro-4-(7-hydroxy-1-trifluoromethyl-3-oxohexahydro-pyrrolo[1,2-c]imidazol-2-yl)-3-fluorobenzonitrile

HRID 501638Notes

Reaction equation

HRID 501638 reaction equation
C(O[C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][Si](C(C)(C)C)(C)C)[C@H:9]1[C@@H:21](O)[C:22]([F:25])([F:24])[F:23])=[O:7])(C)(C)C.[N:27]([C:30]1[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[C:32]([Cl:38])[C:31]=1[F:39])=C=O>>[Cl:38][C:32]1[C:31]([F:39])=[C:30]([N:27]2[C@H:21]([C:22]([F:23])([F:24])[F:25])[C@@H:9]3[C@H:10]([OH:13])[CH2:11][CH2:12][N:8]3[C:6]2=[O:7])[CH:37]=[CH:36][C:33]=1[C:34]#[N:35]

Participants

3

Reactant 2

HCID 16732286(2R,3R)-3-(tert-Butyl-dimethylsilanyloxy)-2-[(1R)-(2,2,2-trifluoro-1-hydroxyethyl)]pyrrolidine-1-carboxylic acid tert-butyl esterHCID 597542814-Isocyanato-3-fluoro-2-chlorobenzonitrile

Product 1

HCID 59754245(1S,7R,7aR)-2-Chloro-4-(7-hydroxy-1-trifluoromethyl-3-oxohexahydro-pyrrolo[1,2-c]imidazol-2-yl)-3-fluorobenzonitrile

Procedure

The title compound was prepared from (2R,3R)-3-(tert-butyl-dimethylsilanyloxy)-2-[(1R)-(2,2,2-trifluoro-1-hydroxyethyl)]pyrrolidine-1-carboxylic acid tert-butyl ester (66A) and 2-chloro-4-isocyanato-3-fluorobenzonitrile (73C) following procedures analogous to those found in Example 72. LCMS: m/z 364[M+H]+

Sources & evidence

ORD record
ord-fc85a4ab8cbe402b8cb2cfdf1c6ca6fa
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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