Dichloromethane → (3S)-1-(4-Chlorobenzyl)-7-cyclohexyl-3-fluoro-1,7-diazaspiro[4.4]nonan-6-one

HRID 1672396Notes

Reaction equation

HRID 1672396 reaction equation
C(N(S(F)(F)[F:7])CC)C.[Cl:10][C:11]1[CH:34]=[CH:33][C:14]([CH2:15][N:16]2[C:20]3([CH2:24][CH2:23][N:22]([CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)[C:21]3=[O:31])[CH2:19][C@@H:18](O)[CH2:17]2)=[CH:13][CH:12]=1.C(Cl)Cl>>[Cl:10][C:11]1[CH:34]=[CH:33][C:14]([CH2:15][N:16]2[C:20]3([CH2:24][CH2:23][N:22]([CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)[C:21]3=[O:31])[CH2:19][C@H:18]([F:7])[CH2:17]2)=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 123472(Diethylamino)sulfur trifluorideHCID 24759088(3R)-1-(4-chlorobenzyl)-7-cyclohexyl-3-hydroxy-1,7-diazaspiro[4.4]nonan-6-one

Product 1

HCID 67355909(3S)-1-(4-Chlorobenzyl)-7-cyclohexyl-3-fluoro-1,7-diazaspiro[4.4]nonan-6-one

Procedure

Diethylaminosulfur trifluoride (11 μL, 0.000083 mol) was added to a solution of (3R)-1-(4-chlorobenzyl)-7-cyclohexyl-3-hydroxy-1,7-diazaspiro[4.4]nonan-6-one (10.0 mg, 0.0000276 mol; prepared as in Example 32, derived from peak 2 of step 2) in DCM (1.0 mL, 0.016 mol) at −78° C. The mixture was allowed to gradually warm to RT and stirred for 2 h. The crude reaction mixture was purified by prep. HPLC to afford the desired product. LC/MS: 365.1 (M+1H)+.

Workup

  1. customThe crude reaction mixture
  2. customwas purified by prep

Sources & evidence

ORD record
ord-c2d226fd92bb478f9211b4ba825fc963
Source dataset
uspto-grants-2011_08
Patent number
US07998959B2

Reaction notes

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