Acetonitrile → HCID 178501357, compound

HRID 535088

Reaction equation

HRID 535088 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[C@@H:10]([C:11]([N:13]2[CH2:17][CH2:16][C@H:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:14]2)=[O:12])[CH2:9][CH2:8][NH:7][CH2:6]1)=[O:4].C(#N)C.C(N(CC)CC)C.[CH:34]1[CH:39]=[CH:38][C:37]([O:40][C:41](OC2C=CC=CC=2)=[N:42][C:43]#[N:44])=[CH:36][CH:35]=1>>[C:43](/[N:42]=[C:41](\[O:40][C:37]1[CH:38]=[CH:39][CH:34]=[CH:35][CH:36]=1)/[N:7]1[CH2:8][CH2:9][C@H:10]([C:11]([N:13]2[CH2:17][CH2:16][C@H:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:14]2)=[O:12])[C@@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6]1)#[N:44]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 688090Diphenyl N-CyanocarbonimidateHCID 67304902(3r,4s)-4-((r)-3-Phenyl-pyrrolidine-1-carbonyl)-piperidine-3-carboxylic acid methyl ester

Product 1

HCID 178501357HCID 178501357, compoundYield 88.2%

Conditions

Temperature
85 °C

Procedure

To a stirred solution of (3R,4S)-4-((R)-3-Phenyl-pyrrolidine-1-carbonyl)-piperidine-3-carboxylic acid methyl ester (654 mg, 0.00207 mol) in anhydrous acetonitrile (11.0 mL, 0.211 mol) at rt was added triethylamine (0.579 mL, 0.00413 mol) and diphenyl cyanocarbonimidate (762 mg, 0.00310 mol). The reaction mixture was heated to reflux (oil bath temperature: 85° C.) for 18 h. The reaction mixture was concentrated in vacuo. The residue was purified by Combiflash with 40-90% EtOAc/Hex to give the product as a colorless solid (841 mg, 88% in yield). MS (ESI): (M+H)+=461.1.

Workup

  1. temperatureThe reaction mixture was heated
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe residue was purified by Combiflash with 40-90% EtOAc/Hex

Sources & evidence

ORD record
ord-3985aa424dd74423a910ecf8e93e496a
Source dataset
uspto-grants-2014_10
Patent number
US08853243B2

Linked notes

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