Benzhydrylpiperazine → HCID 131724628, compound

HRID 393985Notes

Reaction equation

HRID 393985 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:9]1[C:19](O)=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]1([CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([N:44](CC)C(C)C)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH:28]([N:29]1[CH2:30][CH2:31][N:32]([NH:44][C:19]([C@@H:9]2[CH:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][CH2:12][N:8]2[C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])=[O:20])[CH2:33][CH2:34]1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 70048BenzhydrylpiperazineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 23531924HCID 23531924, compound

Product 1

HCID 131724628HCID 131724628, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(tert-Butoxycarbonyl)-3-phenyl-[(2S)-2-pyrrolidinecarboxylic acid] (14) (1.50 g; 5.1 mmol) prepared according to Chung, J. Y. et al., J. Org Chem. 55:270-5 (1990) is dissolved in methylene chloride (55 mL) at ambient temperature. 1-(Diphenylmethyl)piperazine (1.62 g; 6.4 mmol), N,N-diisopropylethylamine (1.50 g; 2.25 mmol) and PyBOP (3.35 g; 6.4 mmol) are added sequentially. The reaction is stirred for 18 hours at room temperature, then concentrated under reduced pressure. The residue is purified via silica gel chromatography (33%→50% ethyl acetate in hexanes) affording the desired product as a white solid. CIMS: MH+ 526

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue is purified via silica gel chromatography (33%→50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-1571c08fa5fb4ba490c2273826555b1a
Source dataset
uspto-grants-2004_10
Patent number
US06809093B2

Reaction notes

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