Hydrochloric Acid → 8-Azabicyclo[3.2.1]octan-3-ylmethanol

HRID 1849585Notes

Reaction equation

HRID 1849585 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:9][C@H:8]2[N:10](C(OC(C)(C)C)=O)[C@H:5]([CH2:6][CH2:7]2)[CH2:4]1.Cl>O1CCOCC1>[CH:8]12[NH:10][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]([CH2:2][OH:1])[CH2:9]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 50999116Exo-8-boc-8-azabicyclo[3.2.1]octane-3-methanol

Product 1

HCID 457926978-Azabicyclo[3.2.1]octan-3-ylmethanolYield 57.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of (1R,5S)-tert-butyl 3-(hydroxymethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate (0.9 g, 3.7 mmol) and HCl in dioxane (2 N, 5.0 mL) was stirred at room temperature for 2 h. The mixture was concentrated in vacuo to afford the desired product (300 mg crude), which was used in the next step without further purification. LCMS (ESI) m/z: 139.7 [M−H]−.

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-0f86d8ab44af48689ff9fb0bd1f677d9
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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