Hydrochloric Acid → HCID 86583534, compound

HRID 1016760Notes

Reaction equation

HRID 1016760 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:15]2[CH:20]=[C:19]([CH:21]=[CH2:22])[CH:18]=[C:17]([CH:23]=O)[CH:16]=2)[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1)#[N:2].[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1.[Na].Cl>CO.C(O)(=O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:15]2[CH:20]=[C:19]([CH:21]=[CH2:22])[CH:18]=[C:17]([CH2:23][N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:16]=2)[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 5360545SodiumHCID 86583532HCID 86583532, compound

Product 1

HCID 86583534HCID 86583534, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Eine suspension von 200 mg of the aldehyde described in Example 80.1 and 0.062 ml of pyrrolidine in 2 ml of MeOH was adjusted to pH 6 by the dropwise addition of acetic acid. Then, 46 mg of sodium cyanoborhydride were added and the mixture was stirred overnight at room temperature. It was acidified to pH 3 with 1N HCl and subsequently evaporated. The crude product was isolated by extraction and purified by chromatography on silica gel gereinigt. There were obtained 200 mg of methyl (RS)-(4-cyano-phenylamino)-(3-pyrrolidin-1-ylmethyl-5-vinyl-phenyl)-acetate as a colorless oil.

Workup

  1. customsubsequently evaporated
  2. customThe crude product was isolated by extraction
  3. custompurified by chromatography on silica gel gereinigt

Sources & evidence

ORD record
ord-d89e417ba6d9460db5fdbe74a778be2c
Source dataset
uspto-grants-2002_11
Patent number
US06476264B2

Reaction notes

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