Methanol → (2S)-(-)-1-(4-indolyloxy)-3-(4-(2-fluorophenyl)piperidin-1-yl)-2-propanol ethanedioate

HRID 1900954Notes

Reaction equation

HRID 1900954 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2.[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.[C:28]([OH:33])(=[O:32])[C:29]([OH:31])=[O:30].CO>C(OCC)(=O)C>[C:28]([OH:33])(=[O:32])[C:29]([OH:31])=[O:30].[NH:10]1[C:11]2[C:7](=[C:6]([O:5][CH2:4][C@@H:2]([OH:1])[CH2:3][N:25]3[CH2:26][CH2:27][CH:22]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[F:15])[CH2:23][CH2:24]3)[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

Participants

6

Reactant 4

HCID 887MethanolHCID 971Oxalic AcidHCID 10943254(2s)-Glycidyl indol-4-yl etherHCID 212683544-(2-Fluorophenyl)Piperidine

Product 1

HCID 131719699(2S)-(-)-1-(4-indolyloxy)-3-(4-(2-fluorophenyl)piperidin-1-yl)-2-propanol ethanedioate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The title compound was prepared in similar fashion from (S)-(+)-4-(oxiranylmethoxy)-1H-indole and 4-(2-fluorophenyl)piperidine. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 40% overall yield. FDMS m/e=368 (M+ of free base). α[D]589 =-12.31 (c=0.61, methanol).

Sources & evidence

ORD record
ord-1deb342c34f849dcb53724f03227ac80
Source dataset
uspto-grants-1996_11
Patent number
US05576321

Reaction notes

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