(2R)-2-(Aminomethyl)-4-(2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-pentanol → (2S)-2-(Aminomethyl)-4-(2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-pentanol

HRID 418788Notes

Reaction equation

HRID 418788 reaction equation
[NH2:1][CH2:2][C@:3]([OH:21])([CH2:8][C:9]([C:12]1[C:20]2[O:19][CH2:18][CH2:17][C:16]=2[CH:15]=[CH:14][CH:13]=1)([CH3:11])[CH3:10])[C:4]([F:7])([F:6])[F:5].O1C2C(C(C)(C)C[C@@](CN[C@@H](C3C=CC=CC=3)C)(O)C(F)(F)F)=CC=CC=2CC1>>[NH2:1][CH2:2][C@@:3]([OH:21])([CH2:8][C:9]([C:12]1[C:20]2[O:19][CH2:18][CH2:17][C:16]=2[CH:15]=[CH:14][CH:13]=1)([CH3:11])[CH3:10])[C:4]([F:6])([F:7])[F:5]

Participants

3

Reactant 2

HCID 57615952(2R)-2-(Aminomethyl)-4-(2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-pentanolHCID 66648717(2S)-4-(2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-({[(1R)-1-phenylethyl]amino}methyl)-2-pentanol2×

Product 1

HCID 15605604(2S)-2-(Aminomethyl)-4-(2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-pentanol

Procedure

Similarly prepared to Intermediate 24 by hydrogenolysis of (2S)-4-(2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-({[(1R)-1-phenylethyl]amino}methyl)-2-pentanol (Intermediate 22).

Sources & evidence

ORD record
ord-b8ed9b4e5f1a464d81254bb246184fe0
Source dataset
uspto-grants-2012_01
Patent number
US08093281B2

Reaction notes

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