(R)-5-Bromo-3-(1-methyl-2-pyrrolidinyl methyl)-1H-indole → 5-Bromo-N,N-Dimethyltryptamine

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C@H:12]1CC[CH2:14][N:13]1[CH3:17].C(OC(N1C2C(=CC(Br)=CC=2)C=C1C(C1CCCN1)=O)=O)C1C=CC=CC=1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][N:13]([CH3:14])[CH3:17]

Participants

Reactant 2

HCID 11185464(R)-5-Bromo-3-(1-methyl-2-pyrrolidinyl methyl)-1H-indole

HCID 86754906N-benzyloxycarbonylpyrrolidin-2-ylcarbonyl5-bromo-1H-indole

Product 1

HCID 3602525-Bromo-N,N-Dimethyltryptamine

Procedure

(R)-5-Bromo-3-[(N-methylpyrrolidin-2-yl)methyl]-1H-indole: (63%) from (R)-3-(N-benzyloxycarbonylpyrrolidin-2-ylcarbonyl5-bromo-1H-indole (Example 2a).

Sources & evidence

ORD record: ord-04b8a24d45734fa489d7c8216e35c848
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998438

Reaction notes

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