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

HRID 710316Notes

Reaction equation

HRID 710316 reaction equation
C(OC(=O)[NH:7][C:8]1([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][N:27]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:29]([C:36](=[O:41])[C:37]([F:40])([F:39])[F:38])=[CH:28]3)=[CH:20][CH:19]=2)[CH2:13][O:12]C(C)(C)[O:10][CH2:9]1)(C)(C)C.C(Cl)Cl.Cl>CO>[NH2:7][C:8]([CH2:9][OH:10])([CH2:13][OH:12])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][N:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29]([C:36](=[O:41])[C:37]([F:38])([F:39])[F:40])=[CH:28]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 131733935tert-Butyl-2,2-dimethyl-5-(4-(3-(3-(2,2,2-trifluoroacetyl)-1H-indol-1-yl)propyl)phenethyl)-1,3-dioxan-5-ylcarbamate

Product 1

HCID 461948891-(1-(3-(4-(3-Amino-4-hydroxy-3-(hydroxymethyl)butyl)phenyl)propyl)-1H-indol-3-yl)-2,2,2-trifluoroethanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  1. distillationThe solvent was distilled
  2. customto give the product (0.01 g; 69%)

Sources & evidence

ORD record
ord-8d3a5d094add489f80d06800a8e01aaf
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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