(6-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-((2R,6S)-2,6-dimethylmorpholino)-3-fluoropyridin-2-yl)(1-methyl-1H-imidazol-2-yl)methanol → (6-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-((2R,6S)-2,6-dimethylmorpholino)-3-fluoropyridin-2-yl)(1-methyl-1H-imidazol-2-yl)methanone

HRID 577859Notes

Reaction equation

HRID 577859 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[N:25]=[C:24]([CH:26]([C:28]2[N:29]([CH3:33])[CH:30]=[CH:31][N:32]=2)[OH:27])[C:23]([F:34])=[C:22]([Cl:35])[C:21]=1[N:36]1[CH2:41][C@H:40]([CH3:42])[O:39][C@H:38]([CH3:43])[CH2:37]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([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>ClCCl.[O-2].[Mn+4].[O-2]>[Si:1]([O:18][CH2:19][C:20]1[N:25]=[C:24]([C:26]([C:28]2[N:29]([CH3:33])[CH:30]=[CH:31][N:32]=2)=[O:27])[C:23]([F:34])=[C:22]([Cl:35])[C:21]=1[N:36]1[CH2:37][C@H:38]([CH3:43])[O:39][C@H:40]([CH3:42])[CH2:41]1)([C:14]([CH3:15])([CH3:17])[CH3:16])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 67357736(6-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-((2R,6S)-2,6-dimethylmorpholino)-3-fluoropyridin-2-yl)(1-methyl-1H-imidazol-2-yl)methanol2×

Product 1

HCID 67376639(6-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-((2R,6S)-2,6-dimethylmorpholino)-3-fluoropyridin-2-yl)(1-methyl-1H-imidazol-2-yl)methanoneYield 84%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of (6-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-((2R,6S)-2,6-dimethylmorpholino)-3-fluoropyridin-2-yl)(1-methyl-1H-imidazol-2-yl)methanol (1.2 g, 1.93 mmol, Intermediate 73) in dichloromethane (20 mL) was added Manganese (IV) oxide (0.670 g, 7.70 mmol). The mixture was allowed to stir overnight at room temperature. The reaction was filtered through Celite®, and the filtrate concentrated under vacuum to give clear oil. The oil was purified on short bed of silica using 20-30% ethyl acetate in n-hexane to give 1.0 g (84%) the title compound as oil.

Workup

  1. filtrationThe reaction was filtered through Celite®
  2. concentrationthe filtrate concentrated under vacuum
  3. customto give clear oil
  4. customThe oil was purified on short bed of silica using 20-30% ethyl acetate in n-hexane

Sources & evidence

ORD record
ord-62963422ac804924ba0feb2d3c42549b
Source dataset
uspto-grants-2015_05
Patent number
US09040528B2

Reaction notes

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