Water → HCID 86607602, compound

HRID 1244730Notes

Reaction equation

HRID 1244730 reaction equation
C[N:2]([C@@H:10]1[C:18]2[C:13](=CC=CC=2)C[C@@H]1OC1CCCCO1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[C:26]1([CH3:36])[CH:31]=[CH:30][C:29](S(O)(=O)=O)=[CH:28][CH:27]=1.C([O-])(O)=[O:38].[Na+].O>CO.C(OCC)(=O)C>[C:5]([O:4][C:3](=[O:9])[NH:2][CH2:10][C@H:18]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:36][C@@H:13]1[OH:38])([CH3:6])([CH3:7])[CH3:8]

Participants

7

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 69845023HCID 69845023, compound

Product 1

HCID 86607602HCID 86607602, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl methyl[(1R,2S)-2-(tetrahydro-2H-pyran-2-yloxy)-2,3-dihydro-1H-inden-1-yl]carbamate (Method 16; 4.0 g, 11.5 mmol) was dissolved in methanol (50 mL), 4-toluene sulphonic acid added and the reaction stirred at ambient temperature for 2 hours. Saturated NaHCO3 (50 mL), water (100 mL) was added and ethyl acetate (100 mL) was added and the mixture stirred for 30 mins. The organic phase was separated, washed with water (50 mL), brine (50 mL) and dried (MgSO4). The volatiles were removed by evaporation under reduced pressure to give the title compound (3.0 g, 99%) as an oil.

Workup

  1. stirringthe mixture stirred for 30 mins
  2. customThe organic phase was separated
  3. washwashed with water (50 mL), brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. customThe volatiles were removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-1ec12d82c074416d828b50440911808e
Source dataset
uspto-grants-2006_10
Patent number
US07122567B2

Reaction notes

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