Hydrochloric Acid → HCID 24782563, compound

HRID 82375Notes

Reaction equation

HRID 82375 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:13]([C:14]([N:16]3[CH2:21][CH2:20][N:19]([C:22]4[C:23]5[C@H:30]([CH3:31])[CH2:29][CH2:28][C:24]=5[N:25]=[CH:26][N:27]=4)[CH2:18][CH2:17]3)=[O:15])[CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[ClH:39].O1CCOCC1>C(Cl)Cl>[ClH:1].[ClH:39].[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[CH2:10][NH:11][CH2:12][C@H:13]2[C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:23]4[C@H:30]([CH3:31])[CH2:29][CH2:28][C:24]=4[N:25]=[CH:26][N:27]=3)[CH2:18][CH2:17]2)=[O:15])[CH:5]=[CH:6][C:7]=1[Cl:8].[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:10][NH:11][CH2:12][C@@H:13]2[C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:23]4[C@H:30]([CH3:31])[CH2:29][CH2:28][C:24]=4[N:25]=[CH:26][N:27]=3)[CH2:18][CH2:17]2)=[O:15])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67340196tert-butyl 3-(3,4-dichlorophenyl)-4-(1-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-4-carbonyl)pyrrolidine-1-carboxylate

Product 2

HCID 24782563HCID 24782563, compoundHCID 67340648HCID 67340648, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the mixture of diastereomers of tert-butyl 3-(3,4-dichlorophenyl)-4-(1-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-4-carbonyl)pyrrolidine-1-carboxylate (34 mg, 0.061 mmol) in DCM (3.1 mL) was added to a 4.0M HCl solution in dioxane (1.1 mL, 4.25 mmol). The mixture was stirred at room temperature overnight. The solvents were removed in vacuo to give ((3S,4R)-4-(3,4-dichlorophenyl)pyrrolidin-3-yl)(4-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)methanone dihydrochloride and ((3R,4S)-4-(3,4-dichlorophenyl)pyrrolidin-3-yl)(4-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)methanone dihydrochloride as a mixture of diastereomers (32 mg, 99%).

Workup

  1. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-a079aef3361646a284b0abcc8f922011
Source dataset
uspto-grants-2014_09
Patent number
US08846681B2

Reaction notes

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