Acetaldehyde → HCID 58312634, compound

HRID 527498Notes

Reaction equation

HRID 527498 reaction equation
[CH2:1]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([F:20])[CH:14]=2)[C@H:10]([NH2:21])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:22](=O)[CH3:23].Cl[C:26]([O:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)=[O:27]>>[F:35][C:32]1[CH:33]=[CH:34][C:29]([O:28][C:26](=[O:27])[N:21]([C@H:10]2[C@H:11]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([F:20])[CH:14]=3)[CH2:12][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9]2)[CH2:22][CH3:23])=[CH:30][CH:31]=1

Participants

4

Reactant 3

HCID 177AcetaldehydeHCID 27332564-Fluorophenyl chloroformateHCID 58312647HCID 58312647, compound

Product 1

HCID 58312634HCID 58312634, compound

Procedure

In analogy to the procedure described for the synthesis of rac-{(3S,4R)-4-(3,4-Dichloro-phenyl)-1-[1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-ethyl-carbamic acid 4-fluoro-phenyl ester (example 1, step g & h) the title compound was prepared from (3S,4R)-1-Benzyl-4-(4-chloro-3-fluoro-phenyl)-pyrrolidin-3-ylamine through reductive amination with acetaldehyde followed by reaction with 4-fluorophenyl chloroformate to yield the title compound as light brown oil. MS m/e: 471.2 [M+H]+.

Sources & evidence

ORD record
ord-e74a0ab0330a4c0ab9dd58fbfa8fc680
Source dataset
uspto-grants-2016_05
Patent number
US09346786B2

Reaction notes

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