1H-imidazole-2-carbaldehyde → (RS)-4-(1H-Imidazol-2-ylmethyl)-3-methyl-3,4-dihydro-2H-benzo[1,4]oxazine

HRID 1172993Notes

Reaction equation

HRID 1172993 reaction equation
[CH3:1][CH:2]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[O:4][CH2:3]1.[NH:12]1[CH:16]=[CH:15][N:14]=[C:13]1[CH:17]=O.C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[NH:12]1[CH:16]=[CH:15][N:14]=[C:13]1[CH2:17][N:7]1[C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[O:4][CH2:3][CH:2]1[CH3:1]

Participants

6

Reactant 3

HCID 249551H-imidazole-2-carbaldehydeHCID 27637603-Methyl-3,4-dihydro-2H-1,4-benzoxazineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 59556803(RS)-4-(1H-Imidazol-2-ylmethyl)-3-methyl-3,4-dihydro-2H-benzo[1,4]oxazine

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

Prepared analogously to Example 1, from (RS)-3-methyl-3,4-dihydro-2H-benzo[1,4]oxazine, imidazole-2-carboxaldehyde, zinc chloride and sodium cyanoborohydride in methanol. MS (ISP): 230.4 ([M+H]+).

Sources & evidence

ORD record
ord-6e0c96ad63f24231ad2bd0eb49a99561
Source dataset
uspto-grants-2010_11
Patent number
US07834044B2

Reaction notes

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