Methanol → (2s)-(-)-1-(4-Indolyloxy)-3-(spiro[1h-indene-1,4'-piperidin]-1'-yl)-2-propanol ethanedioate

HRID 977345Notes

Reaction equation

HRID 977345 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.[NH:15]1[CH2:20][CH2:19][C:18]2([C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21]2)[CH2:17][CH2:16]1.[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31].CO>C(OCC)(=O)C>[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31].[NH:10]1[C:11]2[C:7](=[C:6]([O:5][CH2:4][C@@H:2]([OH:1])[CH2:3][N:15]3[CH2:20][CH2:19][C:18]4([C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH:22]=[CH:21]4)[CH2:17][CH2:16]3)[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

Participants

6

Reactant 4

HCID 887MethanolHCID 971Oxalic AcidHCID 10330052Spiro[indene-1,4'-piperidine]HCID 10943254(2s)-Glycidyl indol-4-yl ether

Product 1

HCID 131719706(2s)-(-)-1-(4-Indolyloxy)-3-(spiro[1h-indene-1,4'-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 spiro[1H-indene-1,4'-piperidine]. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 80% overall yield. mp 119°-120°. FDMS m/e=374 (M+ of free base). α[D]589 =-5.51 (c=0.47, methanol).

Sources & evidence

ORD record
ord-544b3edff5974810821c0b6bf403a341
Source dataset
uspto-grants-1997_03
Patent number
US05614523

Reaction notes

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