Sodium Phosphate, Dibasic → (1R*,2R*,4'S*,5S*)2',3',4',5'-Tetrahydro-4'-[(2RS)-2,3-dihydro-2-methyl-5-trifluoromethoxybenzofuran-7-yl]-1-phenylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan]

HRID 1017285Notes

Reaction equation

HRID 1017285 reaction equation
[CH3:1][CH:2]1[CH2:6][C:5]2[CH:7]=[C:8]([O:38][C:39]([F:42])([F:41])[F:40])[CH:9]=[C:10]([C@H:11]3[CH2:15][O:14][C@:13]4([CH2:21][CH2:20][C@H:19]5[NH:22][C@@:16]4([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH2:17][CH:18]5S(C4C=CC=CC=4)(=O)=O)[CH2:12]3)[C:4]=2[O:3]1.P([O-])([O-])(O)=O.[Na+].[Na+]>[Na].[Hg].CO>[CH3:1][CH:2]1[CH2:6][C:5]2[CH:7]=[C:8]([O:38][C:39]([F:42])([F:40])[F:41])[CH:9]=[C:10]([C@H:11]3[CH2:15][O:14][C@:13]4([CH2:21][CH2:20][C@H:19]5[NH:22][C@@:16]4([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH2:17][CH2:18]5)[CH2:12]3)[C:4]=2[O:3]1

Participants

5

Reactant 2

HCID 24203Sodium Phosphate, DibasicHCID 70152459(1R*,2R*,4'S*,5R*)-2',3',4',5'-Tetrahydro-4'-[(2RS)-2,3-dihydro-2-methyl-5-trifluoromethoxybenzofuran-7-yl]-1-phenyl-6-phenylsulphonylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan]

Product 1

HCID 10204793(1R*,2R*,4'S*,5S*)2',3',4',5'-Tetrahydro-4'-[(2RS)-2,3-dihydro-2-methyl-5-trifluoromethoxybenzofuran-7-yl]-1-phenylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan]Yield 69.5%

Reagents, catalysts & solvents 2

HCID 9837419Sodium amalgamCatalystHCID 887MethanolSolvent

Procedure

Sodium amalgam (10%, 2 g) was added in small portions to stirred mixture of (1R*,2R*,4S*,5R*)-2′,3′,4′,5′-tetrahydro-4′-[(2RS)-2,3-dihydro-2-methyl-5-trifluoromethoxybenzofuran-7-yl]-1-phenyl-6-phenylsulphonylspiro[8-azabicyclo[3.2.1]octane-2,2′-furan] (Example 18; 160 mg, 0.26 mmol), disodium hydrogen orthophosphate (500 mg), methanol (10 ml) at +5° C. After reaction went to completion, the mixture was quenched with saturated aqueous NaHCO3, decanted and extracted into dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (dichloromethane:methanol) to give the title compound (83 mg, 67%).

Workup

  1. customAfter reaction
  2. customthe mixture was quenched with saturated aqueous NaHCO3
  3. customdecanted
  4. extractionextracted into dichloromethane
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (dichloromethane:methanol)

Sources & evidence

ORD record
ord-5dccc05639d1409e83f7d43ac3fc79a0
Source dataset
uspto-grants-2002_11
Patent number
US06479486B2

Reaction notes

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