Methanol → HCID 131719710, compound

HRID 1900967Notes

Reaction equation

HRID 1900967 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.[O:15]=[C:16]1[C:25]2([CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:31][CH3:32])[CH:23]=2)[CH2:18][CH2:17]1.[C:33]([OH:38])(=[O:37])[C:34]([OH:36])=[O:35].CO>C(OCC)(=O)C>[C:33]([OH:38])(=[O:37])[C:34]([OH:36])=[O:35].[NH:10]1[C:11]2[C:7](=[C:6]([O:5][CH2:4][C@@H:2]([OH:1])[CH2:3][N:28]3[CH2:29][CH2:30][C:25]4([C:24]5[C:19](=[CH:20][CH:21]=[C:22]([O:31][CH3:32])[CH:23]=5)[CH2:18][CH2:17][C:16]4=[O:15])[CH2:26][CH2:27]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 21268189HCID 21268189, compound

Product 1

HCID 131719710HCID 131719710, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The title compound was prepared in similar fashion from (S)-(+)-4-(oxiranylmethoxy)-1H-indole and 3,4-dihydro-2-oxo-7-methoxyspiro[naphthalene-1(2H),4'-piperidine]. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 55% overall yield. FDMS m/e=434 (M+ of free base). α[D]589 =-5.55 (c=0.54, methanol).

Sources & evidence

ORD record
ord-88c2b95eee1a418e88facc9b22b41cbf
Source dataset
uspto-grants-1996_11
Patent number
US05576321

Reaction notes

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