Acetic Acid → HCID 18600294, compound

HRID 279938Notes

Reaction equation

HRID 279938 reaction equation
[BH4-].[Na+].C(O)(=O)C.[CH3:7][N:8]1[C@@H:13]2[CH2:14][CH:15]=[C:16]([O:18]C)[CH2:17][C@H:12]2[O:11][CH2:10][CH2:9]1>CO.C(O)C>[CH3:7][N:8]1[C@@H:13]2[CH2:14][CH2:15][C:16](=[O:18])[CH2:17][C@H:12]2[O:11][CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 18600295HCID 18600295, compound

Product 1

HCID 18600294HCID 18600294, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Following the procedure of Example 1, 15.2 g of the above enamine in 150 ml of methanol were reduced with 3.78 g of sodium borohydride in 150 ml of ethanol in the presence of 5.14 ml of glacial acetic acid. The product of the reaction, trans-(±)-4-methyl-7-methoxy-3,4,4a,5,8,8a-hexahydro-2H-[1,4]benzoxazine, was hydrolysed by treatment with acid as in Example 1 to yield trans-(±)-4-methyl-3,4,4a,5,6,7,8,8a-octahydro-2H-[1,4]benzoxazin-7-one. The product was purified from a highly colored impurity by treatment with sodium bisulfite as in Example 1.

Sources & evidence

ORD record
ord-a0951780f6724b0eb75f661ae5731a48
Source dataset
uspto-grants-1986_05
Patent number
US04587336

Reaction notes

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