HCID 66649600, compound → HCID 51003469, compound

HRID 420320Notes

Reaction equation

HRID 420320 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:38]=[CH:39][CH:40]=1)[CH2:8][NH:9][C@@H:10]1[C@@H:15]([OH:16])[C@H:14]([CH2:17][C:18]2[CH:23]=[C:22]([O:24][C@H:25]([CH2:30][O:31][CH3:32])[C:26]([F:29])([F:28])[F:27])[C:21]([N+:33]([O-])=O)=[C:20]([F:36])[CH:19]=2)[CH2:13][S@@:12](=[O:37])[CH2:11]1)([CH3:4])([CH3:3])[CH3:2]>CCO.[Ni]>[NH2:33][C:21]1[C:22]([O:24][C@H:25]([CH2:30][O:31][CH3:32])[C:26]([F:29])([F:27])[F:28])=[CH:23][C:18]([CH2:17][C@H:14]2[C@H:15]([OH:16])[C@@H:10]([NH:9][CH2:8][C:7]3[CH:38]=[CH:39][CH:40]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=3)[CH2:11][S@:12](=[O:37])[CH2:13]2)=[CH:19][C:20]=1[F:36]

Participants

4

Reactant 1

HCID 66649600HCID 66649600, compound

Product 1

HCID 51003469HCID 51003469, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of (1R,3R,4S,5S)-3-(3-tert-butyl-benzylamino)-5-[3-fluoro-4-nitro-5-((R)-2,2,2-tri-fluoro-1-methoxymethyl-ethoxy)-benzyl]-1-oxo-tetrahydro-thiopyran-4-ol (1.34 g, 2.27 mmol) in EtOH (27 mL) was hydrogenated at 1 bar over Ra—Ni at 40° C. for 7 h. Filtration over Celite and charcoal afforded the title compound after evaporation as an amorphous solid: TLC (toluene-ETA 95:5) Rf=0.28; HPLC RtH1=0.86 min; ESIMS [M+H]+=561; 1H NMR (600 MHz, CDCl3): δ 7.34 (s, 1H), 7.24 (m, 2H), 7.12 (m, 1H), 6.72 (s, 1H), 6.63 (d, 1H), 5.08 (s, 1H), 5.00 (s, 1H), 4.57 (s, 2H), 3.80-3.67 (m, 3H), 3.57 (m, 1H), 3.30 (s, 3H), 3.18-3.05 (m, 3H), 2.98 (m, 1H), 2.70 (m, 1H), 2.49-2.23 (m, 5H), 1.25 (s, 9H).

Workup

  1. filtrationFiltration over Celite and charcoal

Sources & evidence

ORD record
ord-78cd5c071af34bfe96c9f704b5e7e324
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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