Methanol → HCID 131719711, compound

HRID 1900968Notes

Reaction equation

HRID 1900968 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:25]3=[CH:26][CH:27]=[CH:28][CH2:29][CH:24]3[CH2:23][CH2:22][O:21]2)[CH2:17][CH2:16]1.[C:30]([OH:35])(=[O:34])[C:31]([OH:33])=[O:32].CO>C(OCC)(=O)C>[C:30]([OH:35])(=[O:34])[C:31]([OH:33])=[O:32].[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:25]5=[CH:26][CH:27]=[CH:28][CH2:29][CH:24]5[CH2:23][CH2:22][O: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 10943254(2s)-Glycidyl indol-4-yl etherHCID 21268197HCID 21268197, compound

Product 1

HCID 131719711HCID 131719711, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The title compound was prepared in similar fashion from (S)-(+)-4-(oxiranylmethoxy)-1H-indole and 1,5-dihydrospiro[4H-2-benzopyran-1,4'-piperidine]. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 58% overall yield. FDMS m/e=392 (M+ of free base). α[D]589 =-23.56 (c=0.51, methanol).

Sources & evidence

ORD record
ord-a0c5de38d8ec45a88968607ffa0b63f7
Source dataset
uspto-grants-1996_11
Patent number
US05576321

Reaction notes

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