Dimethylamine, hydrochloride → HCID 178463443, compound

HRID 335499Notes

Reaction equation

HRID 335499 reaction equation
[CH2:1]([NH:3][C:4]1[S:5][C@H:6]2[O:12][C@H:11]([CH:13]=O)[C@@H:10]([OH:15])[C@H:9]([OH:16])[C@H:7]2[N:8]=1)[CH3:2].Cl.[CH3:18][NH:19][CH3:20].C([BH3-])#N.[Na+].CO.C(Cl)Cl>CO>[CH3:18][N:19]([CH2:13][C@H:11]1[O:12][C@H:6]2[C@H:7]([N:8]=[C:4]([NH:3][CH2:1][CH3:2])[S:5]2)[C@@H:9]([OH:16])[C@@H:10]1[OH:15])[CH3:20]

Participants

6

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 21226129Dichloromethane methanolHCID 86731573HCID 86731573, compound

Product 1

HCID 178463443HCID 178463443, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To (3aR,5S,6S,7R,7aR)-2-(ethylamino)-6,7-dihydroxy-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-5-carbaldehyde (40.00 mg; 0.16 mmol; 1.00 eq.) in MeOH (1.00 ml) was added dimethylamine hydrochloride (15.89 mg; 0.19 mmol; 1.20 eq.), and sodium cyanoborohydride (5.10 mg; 0.08 mmol; 0.50 eq.) in 0.5 mL MeOH. The reaction was stirred at room temperature for 15 min. The desired product was isolated by flash chromatography (KPNH column, 0 to 100% MeOH/DCM, 15CV) to afford (3aR,5R,6S,7R,7aR)-5-[(dimethylamino)methyl]-2-(ethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol (9.6 mg, 21%) as a white solid (once lyophilized).

Sources & evidence

ORD record
ord-11ead563132c4384a52541040c81c933
Source dataset
uspto-grants-2014_11
Patent number
US08884023B2

Reaction notes

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