1,4-Dioxane hydrochloride → HCID 86271856, compound

HRID 2277064Notes

Reaction equation

HRID 2277064 reaction equation
[OH:1][C@@H:2]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C@@H:21]2[CH2:25][CH2:24][CH2:23][N:22]2[CH3:26])[CH:14]=1)[CH2:3][CH2:4][NH:5]C(=O)OC(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[NH2:5][CH2:4][CH2:3][C@H:2]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C@@H:21]2[CH2:25][CH2:24][CH2:23][N:22]2[CH3:26])[CH:14]=1)[OH:1]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 131733444HCID 131733444, compound

Product 1

HCID 86271856HCID 86271856, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl ((R)-3-hydroxy-3-(3-(((S)-1-methylpyrrolidin-2-yl)methoxy)phenyl)propyl)carbamate (0.32 g, 0.87 mmol) in DCM (10 mL) was added HCl/dioxane (4 mL) at 0° C. and the reaction mixture was stirred at rt for 2 h. After completion of the reaction the solvent was removed in vacuo. The compound was purified by prep HPLC to obtain (R)-3-Amino-1-(3-(((S)-1-methylpyrrolidin-2-yl)methoxy)phenyl)propan-1-ol (Example 21) as a yellow semi solid. Yield (0.18 g, 68%); 1H NMR (400 MHz, CD3OD) δ 7.29 (t, J=8.0 Hz, 1H), 7.01-6.97 (m, 2H), 6.89-6.87 (m, 1H), 4.82-4.80 (m, 1H), 4.10-4.04 (m, 2H), 3.10-3.02 (m, 3H), 2.68 (s, 3H), 2.65-2.58 (m, 1H), 2.18-2.15 (m, 1H), 2.03-2.01 (m, 2H), 1.99-1.94 (m, 3H), 1.84-1.77 (m, 1H). MS: m/z 265.22 [M+H]+.

Workup

  1. customAfter completion of the reaction the solvent
  2. customwas removed in vacuo
  3. customThe compound was purified by prep HPLC

Sources & evidence

ORD record
ord-8ac5d59e04cd4c6fa257551e841f68df
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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