3-(Oxiran-2-ylmethoxy)pyridine → (2S)-1-Amino-3-(3-pyridinyloxy)-2-propanol

HRID 1061274Notes

Reaction equation

[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.CO.[NH4+:14]>>[NH2:14][CH2:3][C@H:2]([OH:1])[CH2:4][O:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1

Participants

Reactant 2

HCID 98774203-(Oxiran-2-ylmethoxy)pyridine

HCID 22220579Ammonium methanol

Product 1

HCID 69654939(2S)-1-Amino-3-(3-pyridinyloxy)-2-propanolYield 99.5%

Procedure

A solution of 3-(2-oxiranylmethoxy)pyridine (which was obtained in Example 123) (1.41 g) in 120 mL of saturated ammonium methanol was stirred at 0° C. for two days. The reaction mixture was concentrated to give a yellow semi-solid (1.56 g, 99.5% yield); 1H NMR (400 MHz, DMSO-d6) δ 1.60 (brs, 2H), 2.55-2.59 (m, 1H), 2.61-2.68 (m, 1H), 3.67-3.72 (m, 1H), 3.89-3.93 (m, 1H), 4.00-4.04 (m, 1H), 4.90 (brs, 1H), 7.29-7.32 (m, 1H), 7.36-7.38 (m, 1H), 8.13-8.14 (d, 1H), 8.27 (s, 1H); MS (ES) m/z: 138 (M+); Anal. Calcd. for C7H10N2O: C, 57.13; H, 7.19; N, 16.66. Found: C, 57.83; H, 7.17; N, 18.98.

Workup

concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record: ord-1f8999969f9e47848c7d20a5297503ce
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525202B2

Reaction notes

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