4-Methyloxybenzyl chloride → (S)-1-(4-methoxybenzyl)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione

HRID 2191226Notes

Reaction equation

HRID 2191226 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([S:11]([N:14]3[CH2:18][CH2:17][CH2:16][C@H:15]3[CH2:19][O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:13])=[O:12])=[CH:8][CH:9]=2)[C:4](=[O:27])[C:3]1=[O:28].[CH3:29][O:30][C:31]1[CH:38]=[CH:37][C:34](CCl)=[CH:33][CH:32]=1>>[CH3:29][O:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:1][N:2]2[C:10]3[C:5](=[CH:6][C:7]([S:11]([N:14]4[CH2:18][CH2:17][CH2:16][C@H:15]4[CH2:19][O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)(=[O:12])=[O:13])=[CH:8][CH:9]=3)[C:4](=[O:27])[C:3]2=[O:28])=[CH:33][CH:32]=1

Participants

3

Reactant 2

HCID 699934-Methyloxybenzyl chlorideHCID 52888501-Methyl-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione

Product 1

HCID 9914167(S)-1-(4-methoxybenzyl)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dioneYield 69%

Procedure

(S)-1-(4-Methoxybenzyl)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione (11b) was prepared according to the same procedure for compound 11a, except using 4-methoxybenzyl chloride, and purified with hexanesether (1:3) to afford 175 mg (69%) of 11b as a yellow solid, mp 126.7-128.8° C. 1H NMR (300 MHz, CDCl3) δ 8.00 (s, 1H), 7.95 (dd, J=8.25 Hz, J=2.1 Hz, 1H), 7.28-7.21 (m, 4H), 6.96-6.80 (m, 6H), 4.86 (s, 2H), 4.18-4.11 (m, 1H), 3.97-3.88 (m, 2H), 3.80 (s, 3H), 3.50 (m, 1H), 3.23 (m, 1H), 2.02 (m, 2H), 1.78 (m, 2H). Anal. Calcd for C27H2(N2O6S: C, 64.02, H, 5.17; N, 5.53. Found: C, 64.76, H, 5.24; N, 5.06.

Workup

  1. custom(S)-1-(4-Methoxybenzyl)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione (11b) was prepared
  2. custompurified with hexanesether (1:3)

Sources & evidence

ORD record
ord-78b010d50c0f4d79ba483312b086ed72
Source dataset
uspto-grants-2012_12
Patent number
US08329686B2

Reaction notes

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