Triphenylphosphine → tert-Butyl [3-(7-amino-4,4-dimethyl-8-nitro-1,3-dioxo-3,4-dihydro-1H-isoquinolin-2-yl)propyl]-[2-(3,4-dimethoxyphenyl)ethyl]carbamate

HRID 2253302Notes

Reaction equation

HRID 2253302 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[NH2:15][C:16]1[C:25]([N+:26]([O-:28])=[O:27])=[C:24]2[C:19]([C:20]([CH3:32])([CH3:31])[C:21](=[O:30])[NH:22][C:23]2=[O:29])=[CH:18][CH:17]=1.O[CH2:34][CH2:35][CH2:36][N:37]([CH2:45][CH2:46][C:47]1[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[C:49]([O:55][CH3:56])[CH:48]=1)[C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[NH2:15][C:16]1[C:25]([N+:26]([O-:28])=[O:27])=[C:24]2[C:19]([C:20]([CH3:32])([CH3:31])[C:21](=[O:30])[N:22]([CH2:34][CH2:35][CH2:36][N:37]([CH2:45][CH2:46][C:47]3[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[C:49]([O:55][CH3:56])[CH:48]=3)[C:38](=[O:44])[O:39][C:40]([CH3:42])([CH3:43])[CH3:41])[C:23]2=[O:29])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 111184431,3(2H,4H)-Isoquinolinedione, 7-amino-4,4-dimethyl-8-nitro-HCID 59645489tert-Butyl [3-hydroxypropyl][2-(3,4-dimethoxyphenyl)ethyl]carbamate

Product 1

HCID 59645476tert-Butyl [3-(7-amino-4,4-dimethyl-8-nitro-1,3-dioxo-3,4-dihydro-1H-isoquinolin-2-yl)propyl]-[2-(3,4-dimethoxyphenyl)ethyl]carbamateYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIAD (1.92 mL, 9.75 mmol) was slowly added to an ice-cold solution of 7-amino-4,4-dimethyl-8-nitroisoquinoline-1,3(2H,4H)-dione (2.03 g, 8.14 mmol; prepared according to the method described in DE 3410168), tert-butyl [3-hydroxypropyl][2-(3,4-dimethoxyphenyl)ethyl]carbamate (3.31 g, 9.78 mmol), and PPh3 (2.56 g, 9.76 mmol) in THF (40 mL). The reaction mixture was allowed to warm to room temperature and was stirred at this temperature for 16 h. The mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (40-63μ silica gel, hexane:EtOAc 1:1) to give the title compound (4.29 g, 92% yield).

Workup

  1. customprepared
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue was purified by flash chromatography (40-63μ silica gel, hexane:EtOAc 1:1)

Sources & evidence

ORD record
ord-693008bf6a33482f9e4562b08fdbfb81
Source dataset
uspto-grants-2008_01
Patent number
US07323567B2

Reaction notes

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