1-Chloro-N,N-2-trimethylpropenylamine → 1-(Tert-butoxycarbonyl)indolin-3(R,S)-carboxylic acid (N-methyl)amide

HRID 863314Notes

Reaction equation

HRID 863314 reaction equation
Cl[C:2]([N:6](C)C)=C(C)C.[C:9]([O:13][C:14]([N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]([C:25]([OH:27])=O)[CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>C(Cl)Cl.C(N(CC)CC)C.Cl.CN.CN(C1C=CN=CC=1)C>[CH3:2][NH:6][C:25]([CH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:16]([C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15])[CH2:17]1)=[O:27]

Participants

7

Reactant 2

HCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 196977501-((tert-butoxy)carbonyl)-2,3-dihydro-1H-indole-3-carboxylic acid

Product 1

HCID 766348041-(Tert-butoxycarbonyl)indolin-3(R,S)-carboxylic acid (N-methyl)amide

Reagents, catalysts & solvents 4

HCID 8471TriethylamineCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 6364545Methylamine hydrochlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

0.35 ml of 1-chloro-N,N,2-trimethylpropenylamine is added to a solution of 0.59 g of 1-(tert-butoxycarbonyl)indoline-3(R,S)carboxylic acid in methylene chloride at 0° C. After 30 min, 0.93 ml of triethylamine, 0.23 g of methylamine hydrochloride and 4-DMAP, as a catalyst, are added and the mixture is stirred at room temperature for 3 h. The reaction mixture is then chromatographed directly over 80 g of silica gel (mobile phase J). This gives the title compound: Rf (P)=0.65.

Workup

  1. customThe reaction mixture is then chromatographed directly over 80 g of silica gel (mobile phase J)

Sources & evidence

ORD record
ord-ea1d404c13e04bc2804af8a8251d17f4
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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