Dimethylacetamide → [1-(2-tert-butyloxy-2,3-dihydro-1,3-dioxo-1H-benzo[de]isoquinolin-6-yl)-pyrrolidin-3-yl]-carbamic acid, tert-butyl ester

HRID 278975Notes

Reaction equation

HRID 278975 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:21])[N:7]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:8](=[O:15])[C:9]3[C:14]=2[C:13]=1[CH:12]=[CH:11][CH:10]=3.C(C1CCN(N)C1)([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=O.C[C:36]([N:38]([CH3:40])C)=[O:37]>>[C:17]([O:16][N:7]1[C:6](=[O:21])[C:5]2[CH:4]=[CH:3][C:2]([N:7]3[CH2:6][CH2:5][CH:40]([NH:38][C:36](=[O:37])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:8]3)=[C:13]3[C:14]=2[C:9](=[CH:10][CH:11]=[CH:12]3)[C:8]1=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 3

HCID 31374DimethylacetamideHCID 21876723Tert-butyl 1-aminopyrrolidine-3-carboxylateHCID 226239546-Bromo-2-tert-butyloxy-benzo[de]isoquinoline-1,3-dione

Product 1

HCID 131722279[1-(2-tert-butyloxy-2,3-dihydro-1,3-dioxo-1H-benzo[de]isoquinolin-6-yl)-pyrrolidin-3-yl]-carbamic acid, tert-butyl ester

Conditions

Temperature
120 °C

Procedure

A mixture of 6-bromo-2-tert-butyloxy-2,3-dihydro-1H-benzo[de]isoquinoline-1,3-dione (0.5 g, 1.4 mmol, from Example K2) and 3-Boc-aminopyrrolidine (0.8 g, 4.7 mmol) in DMA (4.0 mL) was heated at 120° C. overnight. The mixture was concentrated, and water was added to give a precipitate, which was filtered to yield 0.6 g of the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. additionwater was added
  3. customto give a precipitate, which
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-253a79e466da4dd2bd3a0307ef8ef9fd
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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