Hydrochloric Acid → (r)-Piperidin-2-ylmethanol hydrochloride

HRID 60300Notes

Reaction equation

HRID 60300 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1C(OC(C)(C)C)=O.[ClH:16]>O1CCOCC1>[ClH:16].[NH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:3]1[CH2:2][OH:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 6933953tert-butyl (2R)-2-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 67247105(r)-Piperidin-2-ylmethanol hydrochlorideYield 100.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of (R)-tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate (840 mg, 3.9 mmol) in 1,4-dioxane (15 mL) was treated with hydrogen chloride (4.0N solution in dioxane, 9.8 mL, 39 mmol), and stirred at ambient temperature for 3 hours. The solvent was evaporated in vacuo to afford the title compound as a white solid (594 mg). 1H NMR (400 MHz, d6-DMSO) δ 8.75 (s, 1H), 4.72 (t, J=5.3, 1H), 3.35 (m, 1H), 3.28-3.15 (m, 3H), 2.72 (m, 1H), 2.59-2.52 (m, 1H), 1.88-1.72 (m, 2H), 1.72-1.53 (m, 2H), 1.16 (m, 1H).

Workup

  1. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-5c9bc136dd124595a5d6f84332c05f9b
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

Loading…