Reserpine → tert-butyl N-(4-bromo-3-methoxyphenyl)carbamate

HRID 251506Notes

Reaction equation

HRID 251506 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[O:9][CH3:10].BrC1C=CC(OC)=C(N[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])C=1.CCCCCCC.C(OCC)(=O)C.CO[C@@H]1[C@@H](C(OC)=O)[C@@H]2[C@@H](CN3[C@H](C2)C2NC4C=C(OC)C=CC=4C=2CC3)C[C@H]1OC(C1C=C(OC)C(OC)=C(OC)C=1)=O>C(#N)C>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:4][C:3]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 5770ReserpineHCID 70182544-Bromo-3-methoxyanilineHCID 17942658Tert-butyl (5-bromo-2-methoxyphenyl)carbamateHCID 21899848Ethylacetate heptane

Product 1

HCID 17942648tert-butyl N-(4-bromo-3-methoxyphenyl)carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound was prepared from 4-bromo-3-methoxyaniline in the manner described for compound (2): 1H NMR (DMSO-d6, 400 MHz) δ 9.46 (s, 1H), 7.4 (d, 1H), 7.35 (s, 1H), 6.95 (d, 1H), 3.78 (s, 3H), 1.48 (s, 9H); TLC (heptane/ethyl acetate 8:2) Rf 0.37; RP-HPLC (Hypersil HyPurity Elite C18, 5 μm, 200 A, 250×4.6 mm; 25-100% acetonitrile-0.1 M ammonium acetate over 25 min, 1 ml/min) tr=18.60 min.

Sources & evidence

ORD record
ord-41ed34840c26430db5ac6e128bf74d76
Source dataset
uspto-grants-2011_01
Patent number
US07863444B2

Reaction notes

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