Hydrochloric Acid → (3R,4R)-4-(4-(Benzyloxy)phenyl)piperidin-3-ol hydrochloride

HRID 1507218Notes

Reaction equation

HRID 1507218 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][C@@H:16]2[OH:28])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:29]>O1CCOCC1>[ClH:29].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[CH2:20][CH2:19][NH:18][CH2:17][C@@H:16]2[OH:28])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 52910991tert-butyl (3R,4R)-4-(4-benzyloxyphenyl)-3-hydroxy-piperidine-1-carboxylate

Product 1

HCID 118207402(3R,4R)-4-(4-(Benzyloxy)phenyl)piperidin-3-ol hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of (3R,4R)-tert-butyl 4-(4-(benzyloxy)phenyl)-3-hydroxypiperidine-1-carboxylate (750 mg, 2 mmol), dioxane (4 mL) and 4.9 mL of 4 M HCl in dioxane was stirred at rt for 2 h. The reaction was then evaporated to dryness to yield 550 mg of (3R,4R)-4-(4-(Benzyloxy)phenyl)piperidin-3-ol hydrochloride which was used without further purification. LCMS (method J) RT 0.70 min, m/z 284 (M+H+).

Workup

  1. customThe reaction was then evaporated to dryness

Sources & evidence

ORD record
ord-cc7ae950661244f688dbcc3d97b42e8f
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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