3,4-dihydro-2H-pyran → HCID 21284016, compound

HRID 2232599Notes

Reaction equation

HRID 2232599 reaction equation
[Br:1][CH2:2][C:3](=[O:12])[CH2:4][C:5]([NH:7][CH2:8][C:9]([NH2:11])=[O:10])=[O:6].[BH4-].[Na+].[O:15]1[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16]1.[H-].[Na+]>>[Br:1][CH2:2][CH:3]([OH:12])[CH2:4][C:5]([NH:7][CH2:8][C:9]([NH2:11])=[O:10])=[O:6].[Br:1][CH2:2][CH:3]([O:12][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][O:15]1)[CH2:4][C:5]([NH:7][CH2:8][C:9]([NH2:11])=[O:10])=[O:6].[O:6]=[C:5]1[CH2:4][CH:3]([CH:20]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH2:2][N:7]1[CH2:8][C:9]([NH2:11])=[O:10]

Participants

7

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 24758Sodium hydrideHCID 4311764Sodium borohydrideHCID 21284021HCID 21284021, compound

Product 3

HCID 21284016HCID 21284016, compoundHCID 21284018HCID 21284018, compoundHCID 21284025HCID 21284025, compound

Procedure

Substitution of glycineamide hydrochloride for glycine methyl ester hydrochloride in the procedure of Example 1 gives 2-(4-bromo-3-oxobutanamido)acetamide and successive reaction of this with sodium borohydride, dihydropyran, and sodium hydride according to the procedures of Examples 2, 5 and 10 gives 2-(4-bromo-3-hydroxybutanamido)acetamide, 2-(4-bromo-3-(tetrahydropyran-2-yloxy)butanamido)acetamide and 2-oxo-4-(tetrahydropyran-2-yl)-1-pyrrolidineacetamide, respectively. Deprotection of the latter compound with pyridinium p-toluenesulphonate in ethanol gives 4-hydroxy-2-oxo-1-pyrrolidineacetamide.

Sources & evidence

ORD record
ord-324043e2f08642ec9c085b909b32ce0e
Source dataset
uspto-grants-1988_11
Patent number
US04788300

Reaction notes

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