Potassium Hydroxide → HCID 4452693, compound

HRID 1003386Notes

Reaction equation

C([C@@H]1CC[C@@H](C)C[C@H]1OCC([O:15][CH2:16][CH:17]1[CH:22]2[O:23][CH:21]2[CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]1)=O)(C)C.[OH-:31].[K+]>>[OH:15][CH2:16][CH:17]1[CH2:18][NH:19][CH2:20][CH:21]([OH:23])[CH:22]1[OH:31]

Participants

Reactant 2

HCID 14797Potassium Hydroxide

HCID 86755278HCID 86755278, compound

Product 1

HCID 4452693HCID 4452693, compoundYield 65%

Procedure

tert-Butyl 3-((1R,2S,5R)-2-isopropyl-5-methyl-1-cyclohexyloxy)acetoxymethyl-4,5-epoxypiperidine-1-carboxylate (0.25 g, 0.59 mmol) and 10% aqueous potassium hydroxide were refluxed for 3h. The reaction mixture was evaporated to dryness in vacuo and purified on a silica gel column (Eluent: isopropyl alkohol /26% ammonium hydroxide (3/1)) to give 5-hydroxymethyl-3,4-piperidinediol as an oil (Yield: 56 mg, 65%).

Workup

customThe reaction mixture was evaporated to dryness in vacuo
custompurified on a silica gel column (Eluent: isopropyl alkohol /26% ammonium hydroxide (3/1))

Sources & evidence

ORD record: ord-a2773e0f54664cd8b70b41316c157d59
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06046214

Reaction notes

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