Hydrochloric Acid → HCID 21362440, compound

HRID 497484Notes

Reaction equation

HRID 497484 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][O:10][C@H:9]1[CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][C@@H:17]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:16]1)(C)(C)C.[ClH:30]>O1CCOCC1>[ClH:30].[ClH:30].[F:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][C@@H:17]2[CH2:18][CH2:19][CH2:20][N:15]([CH2:14][C@H:9]3[C@H:8]([NH2:7])[CH2:13][CH2:12][CH2:11][O:10]3)[CH2:16]2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69747883HCID 69747883, compound

Product 1

HCID 21362440HCID 21362440, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To {(2S,3R)-2-[(S)-3-(4-fluoro-benzyl)-piperidin-1-ylmethyl]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester (33 mg, 0.0813 mmol) was added 4 M hydrogen chloride in dioxane (7 mL). After stirring for one hour, the solution was concentrated in vacuo to give (2S,3R)-2-[(S)-3-(4-fluoro-benzyl)-piperidin-1-ylmethyl]-tetrahydro-pyran-3-ylamine dihydrochloride as a pale yellow residue (30.8 mg, 100%). This residue was dissolved in ethyl acetate and poured into 1N sodium hydroxide (20 mL). The layers were separated, and the resulting aqueous layer was washed with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (20 mL), dried over sodium sulfate, and concentrated in vacuo to yield (2S,3R)-2-[(S)-3-(4-fluoro-benzyl)-piperidin-1-ylmethyl]-tetrahydro-pyran-3-ylamine (24.9 mg, 100%) as a pale yellow oil. MS (APCI), m+/z: (M+H)+=307.4.

Workup

  1. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-6f7415e60c1a449e975f1650e5e4945d
Source dataset
uspto-grants-2005_09
Patent number
US06949546B2

Reaction notes

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