Hydrochloric Acid → (2R,3S)-3-amino-8-[6-(methyloxy)-1,5-naphthyridin-4-yl]-8-azaspiro[4.5]decan-2-ol

HRID 734230Notes

Reaction equation

HRID 734230 reaction equation
[OH:1][C@@H:2]1[CH2:6][C:5]2([CH2:11][CH2:10][N:9]([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[N:20]=4)[N:15]=[CH:14][CH:13]=3)[CH2:8][CH2:7]2)[CH2:4][C@@H:3]1[NH:24][C:25](=[O:31])[O:26]C(C)(C)C.Cl.[O:33]1CCOCC1>CO>[C:25](=[O:31])([O-:33])[O-:26].[NH2:24][C@H:3]1[CH2:4][C:5]2([CH2:11][CH2:10][N:9]([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[N:20]=4)[N:15]=[CH:14][CH:13]=3)[CH2:8][CH2:7]2)[CH2:6][C@H:2]1[OH:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 578429321,1-dimethylethyl {(2S,3R)-3-hydroxy-8-[6-(methyloxy)-1,5-naphthyridin-4-yl]-8-azaspiro[4.5]dec-2-yl}carbamate

Product 2

HCID 19660Carbonate IonHCID 57842930(2R,3S)-3-amino-8-[6-(methyloxy)-1,5-naphthyridin-4-yl]-8-azaspiro[4.5]decan-2-olYield 47.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1,1-dimethylethyl {(2S,3R)-3-hydroxy-8-[6-(methyloxy)-1,5-naphthyridin-4-yl]-8-azaspiro[4.5]dec-2-yl}carbamate (220 mg, 0.514 mmol) in MeOH (5 mL) at 25° C. was added a solution of 4M HCl in dioxane (900 μL, 3.60 mmol). After 12 h, the solution was concentrated and the residue neutralized using excess MP carbonate resin yielding the title compound (80 mg, 47%) as an orange oil: LCMS (ES) m/e 329 (M+H)+.

Workup

  1. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-ad5ccc8dfe8a4d11ae54e17826115da5
Source dataset
uspto-grants-2009_09
Patent number
US07592334B2

Reaction notes

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