Butyl chloroformate → HCID 53244988, compound

HRID 587324Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[C@@H:12]([NH:13][CH3:14])[CH2:11][N:10]([C:15]([CH:17]3[CH2:22][CH2:21][N:20]([C:23]([C:25]4([CH3:28])[CH2:27][CH2:26]4)=[O:24])[CH2:19][CH2:18]3)=[O:16])[CH2:9]2)=[CH:4][CH:3]=1.Cl[C:30]([O:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:31]>>[CH2:33]([O:32][C:30](=[O:31])[N:13]([C@@H:12]1[C@@H:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:9][N:10]([C:15]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([C:25]3([CH3:28])[CH2:27][CH2:26]3)=[O:24])[CH2:19][CH2:18]2)=[O:16])[CH2:11]1)[CH3:14])[CH2:34][CH2:35][CH3:36]

Participants

Reactant 2

HCID 61140Butyl chloroformate

HCID 67234170HCID 67234170, compound

Product 1

HCID 53244988HCID 53244988, compound

Procedure

In analogy to the procedure described for the synthesis of example 2 (step b), the title compound rac-{(3R,4S)-4-(4-chloro-phenyl)-1-[1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-methyl-carbamic acid butyl ester was prepared from rac-{4-[(3S,4R)-3-(4-chloro-phenyl)-4-methylamino-pyrrolidine-1-carbonyl]-piperidin-1-yl}-(1-methyl-cyclopropyl)-methanone instead of rac-{4-[(3S,4R)-3-(3,4-dichloro-phenyl)-4-methylamino-pyrrolidine-1-carbonyl]-piperidin-1-yl}-(1-methyl-cyclopropyl)-methanone using butyl chloroformate instead of 4-fluoro-phenyl chloroformate and was obtained as a light yellow foam. MS m/e: 504.2 [M]+.

Workup

customIn analogy to the procedure described for the synthesis of example 2 (step b)
customwas obtained as a light yellow foam

Sources & evidence

ORD record: ord-f0e9487c054a4d66a8f87f9d7d73585f
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226916B2

Reaction notes

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