2-Chloro-3-ethyl-4-fluorobenzonitrile → rel-2-Chloro-4-[[(1R,2S,3R)-2,3-dihydroxy-2-methyl-cyclopentyl]amino]-3-ethyl-benzonitrile

HRID 245074Notes

Reaction equation

HRID 245074 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][C@@H:4]([O:7][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[C@@:3]1([CH3:26])[OH:25].[Cl:27][C:28]1[C:35]([CH2:36][CH3:37])=[C:34](F)[CH:33]=[CH:32][C:29]=1[C:30]#[N:31]>>[Cl:27][C:28]1[C:35]([CH2:36][CH3:37])=[C:34]([NH:1][C@@H:2]2[CH2:6][CH2:5][C@@H:4]([OH:7])[C@:3]2([OH:25])[CH3:26])[CH:33]=[CH:32][C:29]=1[C:30]#[N:31]

Participants

3

Reactant 2

HCID 579086952-Chloro-3-ethyl-4-fluorobenzonitrileHCID 89510182rel-(1S,2R,5R)-2-amino-5-(tert-butyl(diphenyl)silyl)oxy-1-methyl-cyclopentanol

Product 1

HCID 89754415rel-2-Chloro-4-[[(1R,2S,3R)-2,3-dihydroxy-2-methyl-cyclopentyl]amino]-3-ethyl-benzonitrile

Procedure

The title compound is prepared by essentially following the procedure described in Example 20, using rel-(1S,2R,5R)-2-amino-5-(tert-butyl(diphenyl)silyl)oxy-1-methyl-cyclopentanol and 2-chloro-3-ethyl-4-fluoro-benzonitrile for the substitution reaction followed by TBDPS removal with TBAF. 1H-NMR (400 MHz, DMSO-d6) δ 7.44 (d, J=8.7 Hz, 1H), 6.87 (d, J=9.0 Hz, 1H), 5.74-5.70 (m, 1H), 4.74 (d, J=5.4 Hz, 1H), 4.27 (s, 1H), 3.82-3.79 (m, 1H), 3.58-3.51 (m, 1H), 2.80-2.78 (m, 2H), 2.03-2.02 (m, 1H), 1.88-1.86 (m, 1H), 1.69-1.68 (m, 1H), 1.52-1.51 (m, 1H), 1.01-0.97 (m, 3H), 0.93 (s, 3H). LC-ES/MS m/z 295 (M+1).

Workup

  1. customfor the substitution reaction
  2. customfollowed by TBDPS removal with TBAF

Sources & evidence

ORD record
ord-1fe09e7a91aa464493135ed813f90978
Source dataset
uspto-grants-2014_02
Patent number
US08658693B2

Reaction notes

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