Hydrochloric Acid → 1-(aminomethyl)spiro[2.5]octane-1-carboxylic Acid Hydrochloride

HRID 1796839Notes

Reaction equation

HRID 1796839 reaction equation
C(OC([NH:8][CH2:9][C:10]1([C:18]([OH:20])=[O:19])[C:12]2([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:11]1)=O)(C)(C)C.[ClH:21].CCOCC>O1CCOCC1>[ClH:21].[NH2:8][CH2:9][C:10]1([C:18]([OH:20])=[O:19])[C:12]2([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 118184231-(((tert-Butoxycarbonyl)amino)methyl)spiro[2.5]octane-1-carboxylic acid

Product 1

HCID 102200821-(aminomethyl)spiro[2.5]octane-1-carboxylic Acid HydrochlorideYield 86%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 1-(tert-butoxycarbonylamino-methyl)-spiro[2.5]octane-1-carboxylic acid (200 mg, 0.706 mmol) in 1,4-dioxane (3 mL) was added 4N HCl in 1,4-dioxane (3 mL). The reaction was stirred for 18 hours at room temperature. Ether (20 mL) was added and the precipitate was isolated by vacuum filtration. The solid was dried in a vacuum oven at 48° C. to give 133 mg (86%) of 1-aminomethyl-spiro[2.5]octane-1-carboxylic acid hydrochloride as a white solid: mp 240–242° C.; 1H NMR (300 MHz, D2O) δ 0.92 (d, J=5.2 Hz, 1H), 1.40 (d, J=5.2 Hz, 1H), 1.4–1.6 (m, 10H), 3.12 (d, J=14.0 Hz, 1H), 3.61 (d, J=14.0 Hz, 1H); MS (APCI) m/z 184 [M+H]+. Anal. Calcd. For C10H17NO2—HCl: C, 54.67; H, 8.26; N, 6.38; Cl, 16.14. Found: C, 54.91; H, 8.36; N, 6.25; Cl, 15.99.

Workup

  1. customthe precipitate was isolated by vacuum filtration
  2. customThe solid was dried in a vacuum oven at 48° C.

Sources & evidence

ORD record
ord-e5361dab4f824e35870598745f567a21
Source dataset
uspto-grants-2006_04
Patent number
US07030267B2

Reaction notes

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