Triethylamine → [2-(tert-Butyl-dimethyl-silanyloxymethyl)-pyrrolidin-1-yl]-(2-isocyanato-4,5-dimethoxy-phenyl)-methanone

HRID 33983Notes

Reaction equation

HRID 33983 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[CH:11][C:10]=1[C:19]([N:21]1[CH2:25][CH2:24][CH2:23][CH:22]1[C:26]([CH3:34])([CH3:33])[O:27][SiH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:20].Cl[C:36](Cl)([O:38]C(=O)OC(Cl)(Cl)Cl)Cl>C1(C)C=CC=CC=1>[C:29]([SiH2:28][O:27][C:26]([CH3:34])([CH3:33])[CH:22]1[CH2:23][CH2:24][CH2:25][N:21]1[C:19]([C:10]1[CH:11]=[C:12]([O:17][CH3:18])[C:13]([O:15][CH3:16])=[CH:14][C:9]=1[N:8]=[C:36]=[O:38])=[O:20])([CH3:32])([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 131727079(2-Amino-4,5-dimethoxy-phenyl)-[2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-1-yl]-methanone

Product 1

HCID 131727078[2-(tert-Butyl-dimethyl-silanyloxymethyl)-pyrrolidin-1-yl]-(2-isocyanato-4,5-dimethoxy-phenyl)-methanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of triethylamine (1.35 eq.) in anhydrous toluene was added to the amine (5)(1 eq.) and triphosgene (0.36 eq.) in anhydrous toluene under a N2 atmosphere. The reaction was finished after 2 hours. (monitored by IR, ξNCO 2265 cm1). The product was used without further purification.

Workup

  1. customThe product was used without further purification

Sources & evidence

ORD record
ord-991d658f17934d1fbc2cca2b4c60d86d
Source dataset
uspto-grants-2008_09
Patent number
US07429658B2

Reaction notes

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