Boron Trichloride → HCID 10476225, compound

HRID 2164672Notes

Reaction equation

HRID 2164672 reaction equation
[CH:1]([NH:4][CH2:5][CH:6]1[CH2:10][O:9][C:8]2([CH:18](Br)[CH2:17][CH2:16][C:15]3[N:14]([S:20]([C:23]4[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[CH:13]=[CH:12][C:11]2=3)[O:7]1)([CH3:3])[CH3:2].B(Cl)(Cl)Cl>ClC(Cl)C>[OH:7][CH:6]([CH2:5][NH:4][CH:1]([CH3:3])[CH3:2])[CH2:10][O:9][C:8]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH:12]=[CH:13][N:14]2[S:20]([C:23]1[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=1)(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 12946401HCID 12946401, compound

Product 1

HCID 10476225HCID 10476225, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

To a solution of 4'-isopropylaminomethyl-5-bromo-1-p-toluenesulfonyl-4,5,6,7-tetrahydroindole-4-spiro-2'-[1,3]-dioxolane (100 parts) in dichloroethane (1000 parts) is added a solution of boron trichloride (2 molar equivalents) in dichloroethane (500 parts) at -19° C. The mixture is allowed to warm to room temperature and to stand for 50 hours. The reaction mixture is washed with aqueous sodium hydroxide at pH 10 and water, dried and concentrated. The residue is crystallized from hexane-benzene to give 4-(2-hydroxy-3-isopropylaminopropoxy)-1-p-toluenesulfonyl indole in 71% yield.

Workup

  1. washThe reaction mixture is washed with aqueous sodium hydroxide at pH 10 and water
  2. customdried
  3. concentrationconcentrated
  4. customThe residue is crystallized from hexane-benzene

Sources & evidence

ORD record
ord-cb1308d058e449eca6ede3c04fa7c060
Source dataset
uspto-grants-1985_03
Patent number
US04506079

Reaction notes

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