1,4-Dioxane hydrochloride → (3-Aminotetrahydrofuran-3-yl)methanol hydrochloride

HRID 444789Notes

Reaction equation

HRID 444789 reaction equation
C(OC([NH:8][C:9]1([CH2:14][OH:15])[CH2:13][CH2:12][O:11][CH2:10]1)=O)(C)(C)C.[ClH:16].O1CCOCC1>>[ClH:16].[NH2:8][C:9]1([CH2:14][OH:15])[CH2:13][CH2:12][O:11][CH2:10]1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 581348181,1-Dimethylethyl N-[tetrahydro-3-(hydroxymethyl)-3-furanyl]carbamate

Product 1

HCID 66934855(3-Aminotetrahydrofuran-3-yl)methanol hydrochloride

Procedure

A solution of [3-(tert-butoxycarbonylamino)oxolan-3-yl]methanol (2.50 g, 11.5 mmol) in 4M HCl-dioxane (30 mL) was stirred at room temperature for 2 h. The mixture was concentrated in vacuo and dried to give (3-aminooxolan-3-yl)methanol hydrochloride as a pale brown oil (2.17 g, quant.). 1H-NMR (400 MHz, DMSO-d6) δ 1.89-2.01 (2H, m), 3.51-3.58 (2H, m), 3.66 (2H, s), 3.71-3.76 (1H, m), 3.86-3.92 (1H, m), 8.33 (3H, brs).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customdried

Sources & evidence

ORD record
ord-bbbe74bded32421999e3b1b63ce5066c
Source dataset
uspto-grants-2013_07
Patent number
US08476261B2

Reaction notes

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