1-Methyl-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione → (S)-1-methyl-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione

HRID 2191231Notes

Reaction equation

HRID 2191231 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]C[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].O(C[C@@H]1CCN1S(C1C=C2C(=CC=1)NC(=O)C2=O)(=O)=O)C1C=CC=CC=1>>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([S:11]([N:14]3[CH2:18][CH2:17][C@H:15]3[CH2:19][O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:12])=[O:13])=[CH:8][CH:9]=2)[C:4](=[O:27])[C:3]1=[O:28]

Participants

3

Reactant 2

HCID 52888501-Methyl-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dioneHCID 11624920(S)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione

Product 1

HCID 11509289(S)-1-methyl-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dioneYield 48%

Procedure

(S)-1-Methyl-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione (18a) was prepared according to the same procedure for compound 11a, except using compound 17, and purified with ether to afford 46 mg (48%) of 18a as an orange solid, mp 173.5-174.9° C. 1H NMR (300 MHz, CDCl3) δ 8.04 (m, 2H), 7.24 (m, 2H), 6.94 (m, 2H), 6.79 (m, 2H), 4.46 (m, 1H), 4.10 (m, 2H), 3.86 (m, 2H), 3.25 (m, 3H), 2.30 (m, 2H). Anal. Calcd for C19.N2O5S: C, 59.06, H, 4.70, N, 7.25. Found: C, 58.98, H, 4.75; N, 7.19.

Workup

  1. custom(S)-1-Methyl-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione (18a) was prepared
  2. custompurified with ether

Sources & evidence

ORD record
ord-b0bd12eaf4964a5ea19202e55f6a46d1
Source dataset
uspto-grants-2012_12
Patent number
US08329686B2

Reaction notes

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