1,4-Dioxane hydrochloride → HCID 86271855, compound

HRID 2277065Notes

Reaction equation

HRID 2277065 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C@H:11]([C:13]1[CH:14]=[C:15]([CH:30]=[CH:31][CH:32]=1)[O:16][CH2:17][C@@H:18]1[CH2:22][CH2:21][CH2:20][N:19]1C(OC(C)(C)C)=O)[OH:12])=O)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[NH2:8][CH2:9][CH2:10][C@H:11]([C:13]1[CH:32]=[CH:31][CH:30]=[C:15]([O:16][CH2:17][C@@H:18]2[CH2:22][CH2:21][CH2:20][NH:19]2)[CH:14]=1)[OH:12]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 90405868HCID 90405868, compound

Product 1

HCID 86271855HCID 86271855, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 2-((3-((R)-3-((tert-butoxycarbonyl)amino)-1-hydroxypropyl)phenoxy)methyl)pyrrolidine-1-carboxylate (0.3 g, 0.66 mmol) in DCM (10 mL) was added HCl/dioxane (3 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 residue was purified by prep HPLC to give (R)-3-Amino-1-(3-((S)-pyrrolidin-2-ylmethoxy)phenyl)propan-1-ol (Example 22) as a white solid. Yield (0.18 g, 89%); 1H NMR (400 MHz, CD3OD) δ 7.31 (t, J=8.0 Hz, 1H), 7.07 (s, 1H), 7.03 (d, J=7.6 Hz, 1H), 6.93 (d, J=8.0 Hz, 1H), 4.83-4.82 (m, 1H), 4.35 (dd, J=10.4, 3.2 Hz, 1H), 4.17-4.12 (m, 1H), 4.05-4.03 (m, 1H), 3.39-3.36 (m, 2H), 3.14-3.01 (m, 2H), 2.32-2.18 (m, 1H), 2.16-2.08 (m, 2H), 2.06-1.87 (m, 3H). MS: m/z 251.28 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-681cd36bae1343c89463a3ae10519a8c
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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