Triethylamine → (S)-[1-(2-Benzyloxy-5-cyano-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)-pyrrolidin-3-yl]-carbamic acid, tert-butyl ester

HRID 566982Notes

Reaction equation

HRID 566982 reaction equation
[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[C:21]([C:24]#[N:25])[C:22](Cl)=[C:15]3[C:16]=2[C:11](=[CH:12][CH:13]=[CH:14]3)[C:10]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]([O:31][C:32](=[O:39])[NH:33][C@H:34]1[CH2:38][CH2:37][NH:36][CH2:35]1)([CH3:30])([CH3:29])[CH3:28].C(N(CC)CC)C>C(Cl)(Cl)Cl.CO>[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[C:21]([C:24]#[N:25])[C:22]([N:36]3[CH2:37][CH2:38][C@H:34]([NH:33][C:32](=[O:39])[O:31][C:27]([CH3:29])([CH3:28])[CH3:30])[CH2:35]3)=[C:15]3[C:16]=2[C:11](=[CH:12][CH:13]=[CH:14]3)[C:10]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 226240092-Benzyloxy-6-chloro-5-cyano-benzo[de]isoquinoline-1,3-dione

Product 1

HCID 86756246(S)-[1-(2-Benzyloxy-5-cyano-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)-pyrrolidin-3-yl]-carbamic acid, tert-butyl esterYield 63.9%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Following the procedure of Example B2, 2-benzyloxy-6-chloro-5-cyano-benzo[de]isoquinoline-1,3-dione (0.20 g, 0.55 mmol, from Example A2), (S)-pyrrolidin-3-yl-carbamic acid tert-butyl ester (0.11 g, 0.60 mmol), triethyl amine (0.11 g, 1.1 mmol) were reacted at ambient temperature for 5 hours. Column chromatography of the crude product on silica using chloroform/methanol (20:1) gave 0.18 g of the title compound.

Workup

  1. customwere reacted at ambient temperature for 5 hours

Sources & evidence

ORD record
ord-6424a0d81c7c4706aeab95b4deb87468
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Reaction notes

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