(1R)-(+)-1-(4-Fluorophenyl)ethylamine → HCID 67224135, compound

HRID 1944725Notes

Reaction equation

HRID 1944725 reaction equation
[C:1]([Si:5]([CH3:18])([CH3:17])[O:6][CH:7]1[CH2:12][CH2:11][C:10]([OH:16])([C:13]([OH:15])=O)[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[F:19][C:20]1[CH:25]=[CH:24][C:23]([C@H:26]([NH2:28])[CH3:27])=[CH:22][CH:21]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[F:19][C:20]1[CH:25]=[CH:24][C:23]([C@H:26]([NH:28][C:13]([C:10]2([OH:16])[CH2:9][CH2:8][CH:7]([O:6][Si:5]([C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:18])[CH3:17])[CH2:12][CH2:11]2)=[O:15])[CH3:27])=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 6950187(1R)-(+)-1-(4-Fluorophenyl)ethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58291968HCID 58291968, compound2×

Product 1

HCID 67224135HCID 67224135, compoundYield 44%

Procedure

4-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-cyclohexanecarboxylic acid (Intermediate 79, 1.15 g) and with (R)-1-(4-Fluoro-phenyl)-ethylamine (640 mg) were coupled using the standard HATU coupling procedure as described in Example 1 to yield a 3:2 mixture (A:B) of diastereomers the title compound (44%).

Sources & evidence

ORD record
ord-bd621ed8f3464e9ba854b1ef5a5ffdf4
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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