Hydrochloric Acid → HCID 69885274, compound

HRID 47784Notes

Reaction equation

[ClH:1].[OH:2][C@@H:3]([CH2:20][CH3:21])[C@H:4]([NH:12]C(=O)OC(C)(C)C)[CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1>O1CCOCC1>[ClH:1].[ClH:1].[NH2:12][C@@H:4]([C@@H:3]([OH:2])[CH2:20][CH3:21])[CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 20 °C

Procedure

a solution of 50 cm3 of 4N hydrochloric acid in dioxane is added, with stirring and at a temperature in the region of 20° C., to a solution of 4 g of tert-butyl N-[(1R,2S)-2-hydroxy-1-(4-pyridylmethyl)-butyl]carbamate in 50 cm3 of dioxane. The mixture is stirred at a temperature in the region of 20° C. for 18 hours and is then concentrated under reduced pressure (1 kPa) at a temperature in the region of 60° C. 3.6 g of (2R,3S)-2-amino-1-(4-pyridyl)-3-pentanol dihydrochloride are obtained in the form of a white solid [1H NMR spectrum (300 MHz, (CD3)2SO-d6, δ in ppm): 0.92 (t, J=7.5 Hz: 3H); from 1.30 to 1.65 (mt: 2H); 3.13 (dd, J=14 and 9 Hz: 1H); 3.28 (dd, J=14 and 5 Hz: 1H); 3.52 (mt: 1H); 3.68 (mt: 1H); 8.11 (broad d, J=6.5 Hz: 2H); 8.25 (unresolved complex: 3H); 8.90 (broad d, J=6.5 Hz: 2H)].

Workup

concentrationis then concentrated under reduced pressure (1 kPa) at a temperature in the region of 60° C

Sources & evidence

ORD record: ord-a0ea359cb22c4f61a46b022f2383ab8f
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06699895B2

Reaction notes

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