Isobutyric Acid → HCID 13137001, compound

HRID 851229Notes

Reaction equation

Cl.Cl.[CH2:3]([NH:5][CH:6]([CH3:27])[CH2:7][N:8]1[CH2:13][CH2:12][C:11]2[C:14]3[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[CH:19][C:15]=3[O:16][C:17](=[O:18])[C:10]=2[CH2:9]1)[CH3:4].C([O-])(=O)C.[Na+].[BH4-].[Na+].[CH3:35][CH:36]([CH3:40])[C:37](O)=O>>[CH2:3]([N:5]([CH2:35][CH:36]([CH3:40])[CH3:37])[CH:6]([CH3:27])[CH2:7][N:8]1[CH2:13][CH2:12][C:11]2[C:14]3[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[CH:19][C:15]=3[O:16][C:17](=[O:18])[C:10]=2[CH2:9]1)[CH3:4]

Participants

Reactant 4

HCID 6590Isobutyric Acid

HCID 517045Sodium Acetate

HCID 4311764Sodium borohydride

HCID 13136968HCID 13136968, compound

Product 1

HCID 13137001HCID 13137001, compound

Procedure

Prepared by the method described in Example 73 from 3-[2-(ethylamino)propyl]-1,2,3,4-tetrahydro-8,9-dimethoxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one dihydrochloride (6.7 g, 0.016 moles), sodium acetate (2.6 g, 0.032 moles), sodium borohydride (3.3 g, 0.087 moles), and 2-methylpropionic acid (28.5 g, 0.32 moles) instead of acetic acid. Several recrystallizations from diisopropyl ether yielded the final product as the free base (1.4 g), mp 108°-111° C.

Workup

customPrepared by the method
customSeveral recrystallizations from diisopropyl ether

Sources & evidence

ORD record: ord-f8577219fc3c43cf8a01d174b81a4777
Source dataset: uspto-grants-1983_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04382939

Reaction notes

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