Hydrochloric Acid → 1-(1-(3-(4-(3-Amino-4-hydroxy-3-(hydroxymethyl)butyl)phenyl)propyl)-1H-indol-3-yl)-2,2,2-trifluoroethanone

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Dichloromethane	HCID 6344	—
Reactant	tert-Butyl-2,2-dimethyl-5-(4-(3-(3-(2,2,2-trifluoroacetyl)-1H-indol-1-yl)propyl)phenethyl)-1,3-dioxan-5-ylcarbamate	HCID 131733935	—
Solvent	Methanol	HCID 887	—
Product	1-(1-(3-(4-(3-Amino-4-hydroxy-3-(hydroxymethyl)butyl)phenyl)propyl)-1H-indol-3-yl)-2,2,2-trifluoroethanone	HCID 46194889	—

Reaction Steps

A solution of the product of Step E (0.15 g, 0.03 mmol) in a mixture of MeOH, CH2Cl2 and 30% HCl (1 ml, 3 ml, 15 drops respectively) was stirred at room temperature for 3 h. The solvent was distilled and co-distilled with iso-propanol (iPrOH), to give the product (0.01 g; 69%), as colourless solid. 1H-NMR (CDCl3) 1.89-1.92 (m, 2H); 2.12-2.22 (m, 2H); 2.53-2.61 (b, 4H); 3.65-3.75 (m, 4H); 4.13 (tr, 2H, J=7.02 Hz); 6.97 (d, 2H, J=7.71 Hz); 7.07 (d, 2H, J=7.8 Hz); 7.28-7.32 (m, 3H); 7.82 (s, 1H); 8.28-8.31 (m, 1H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09181182B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-8d3a5d094add489f80d06800a8e01aaf
Source note	uspto-grants-2015_11