Methanol → HCID 131719696, compound

HRID 1900951Notes

Reaction equation

HRID 1900951 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.[CH2:15]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH2:19][CH2:18][NH:17][CH2:16]1.[C:26]([OH:31])(=[O:30])[C:27]([OH:29])=[O:28].CO>C(OCC)(=O)C>[C:26]([OH:31])(=[O:30])[C:27]([OH:29])=[O:28].[NH:10]1[C:11]2[C:7](=[C:6]([O:5][CH2:4][C@@H:2]([OH:1])[CH2:3][N:17]3[CH2:16][CH2:15][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[CH2:19][CH2:18]3)[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

Participants

6

Reactant 4

HCID 887MethanolHCID 971Oxalic AcidHCID 14002432,3,4,5-Tetrahydro-1H-benzo(d)azepineHCID 10943254(2s)-Glycidyl indol-4-yl ether

Product 1

HCID 131719696HCID 131719696, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The title compound was prepared in similar fashion from (S)-(+)-4-(oxiranylmethoxy)-1H-indole and 2,3,4,5-tetrahydro-1H-3-benzazepine. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 73% overall yield. FDMS m/e=336 (M+ of free base). α[D]589 =-14.17 (c=0.61, methanol).

Sources & evidence

ORD record
ord-1954993a70d44836912356e13ad1a04b
Source dataset
uspto-grants-1996_11
Patent number
US05576321

Reaction notes

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