Hydrochloric Acid → (S)-2-amino-1-(2-phenyl-[1,3]dithian-2-yl)-hexan-1-ol

HRID 2212226Notes

Reaction equation

C(OC(=O)[NH:7][CH:8]([CH:13]([OH:26])[C:14]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[S:19][CH2:18][CH2:17][CH2:16][S:15]1)[CH2:9][CH2:10][CH2:11][CH3:12])(C)(C)C.Cl>O1CCOCC1.C1(C)C=CC=CC=1>[NH2:7][CH:8]([CH2:9][CH2:10][CH2:11][CH3:12])[C@@H:13]([C:14]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[S:15][CH2:16][CH2:17][CH2:18][S:19]1)[OH:26]

Participants

Conditions

Temperature: 23 °C

Procedure

To {1-[hydroxy-(2-phenyl-[1,3]dithian-2-yl)-methyl]-pentyl}-carbamic acid tert-butyl ester (608 mg, 1.47 mmol) in dioxane (2.7 mL) at 10° C. was added hydrochloric acid (2.7 mL, 4 M in dioxane). The solution was warmed to 23° C. After 3 h, the solution was diluted with toluene (5 mL) and concentrated under reduced pressure. The gummy solid was washed with diethyl ether resulting in the hydrochloride salt of 2-amino-1-(2-phenyl-[1,3]dithian-2-yl)-hexan-1-ol, 414 mg, 82% as a free flowing solid after removal of excess ether under reduced pressure.

Workup

concentrationconcentrated under reduced pressure
washThe gummy solid was washed with diethyl ether resulting in the hydrochloride salt of 2-amino-1-(2-phenyl-[1,3]dithian-2-yl)-hexan-1-ol, 414 mg, 82% as
customafter removal of excess ether under reduced pressure

Sources & evidence

ORD record: ord-b79caf9c24144dd181f083e3b4047e50
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101880B2

Reaction notes

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