Indoline → HCID 68904189, compound

HRID 1869248Notes

Reaction equation

HRID 1869248 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]2[O:10][C@@H:9]2[CH2:11][OH:12])[CH:5]=[CH:6][CH:7]=1.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1>>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14]2)[C@H:9]([OH:10])[CH2:11][OH:12])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 10328IndolineHCID 53713056HCID 53713056, compound

Product 1

HCID 68904189HCID 68904189, compoundYield 73.4%

Procedure

[(2R,3R)-3-(3-chlorophenyl)oxiran-2-yl]methanol (4.8 g, 26 mmol) and indoline (d 1.063, 2.9 mL, 26 mmol) were heated neat at 135° C. in a sealed flask. After 1.5 hours, the cooled mixture was pre-adsorbed on silica gel (25 g). Flash column chromatography (silica 375 g, 20%, 40%, 80% ethyl acetate/hexanes) provided (2S,3S)-3-(3-chlorophenyl)-3-(2,3-dihydro-1H-indol-1-yl)propane-1,2-diol (5.8 g, 73%) as a white solid. MS (ES) m/z 304 ([M+H]+).

Sources & evidence

ORD record
ord-6c0ba291a8614a7dba5d69898811cd97
Source dataset
uspto-grants-2009_12
Patent number
US07638512B2

Reaction notes

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