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

HRID 1444574Notes

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][C@@H:8]([CH2:9][CH2:10][CH2:11][CH3:12])[CH: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(8)-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(8)-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-6a7deb8d72f3406f814f388e59b807c3
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662849B2

Reaction notes

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