Acetic Acid → HCID 67047577, compound

HRID 1429012Notes

Reaction equation

HRID 1429012 reaction equation
[CH:1]([C@H:14]1[CH2:19][C@H:18]([NH2:20])[CH2:17][CH2:16][O:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1.C(O)(=O)C.[BH3-]C#N.[Na+]>>[CH:1]([C@H:14]1[CH2:19][C@H:18]([NH:20][CH2:26][C:25]2[CH:28]=[CH:29][C:22]([F:21])=[CH:23][CH:24]=2)[CH2:17][CH2:16][O:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 680234-FluorobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 66631491HCID 66631491, compound

Product 1

HCID 67047577HCID 67047577, compoundYield 54%

Procedure

trans-4-Amino-2-diphenylmethylpyran 6b (0.24 g, 0.90 mmol) was reacted with 4-fluorobenzaldehyde (0.11 g, 0.90 mmol) in presence of acetic acid (0.05 g, 0.9 mmol), and then reduced with NaCNBH3 (0.07 g, 1.08 mmol) to yield compound 7b (0.18 g, 54%) (Procedure D).

Sources & evidence

ORD record
ord-43b259c16486419fb9e1a2aade6d20ed
Source dataset
uspto-grants-2015_01
Patent number
US08937189B2

Reaction notes

Loading…