3,4-dihydro-2H-pyran → (1R,2S)-1-[(1,1-dimethylethoxy)carbonylamino]-2-[(tetrahydropyran-2-yl)oxy]indan

HRID 1244731Notes

Reaction equation

HRID 1244731 reaction equation
[OH:1][C@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].[O:19]1[CH:24]=[CH:23][CH2:22][CH2:21][CH2:20]1>C(Cl)Cl.C(OCC)(=O)C.[NH+]1C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1>[O:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[O:1][C@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16]

Participants

6

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 17998891tert-Butyl ((1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl)carbamate

Product 1

HCID 69847500(1R,2S)-1-[(1,1-dimethylethoxy)carbonylamino]-2-[(tetrahydropyran-2-yl)oxy]indanYield 95%

Reagents, catalysts & solvents 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl [(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]carbamate (Method 15, 7.0 g, 28.1 mmol) and 3,4-dihydro-2H-pyran (4.7 g, 56.2 mmol) dissolved in DCM (50 mL). 4-Toluene sulphonic acid pyridinium salt (100 mg) was added and the reaction stirred for 4 hours at ambient temperature. The reaction was diluted with ethyl acetate (100 mL), washed with water (2×50 mL), brine (50 mL) and dried (MgSO4). The volatiles were removed by evaporation under reduced pressure to give the title compound (8.9 g, 95%) as an oil.

Workup

  1. washwashed with water (2×50 mL), brine (50 mL)
  2. dry with materialdried (MgSO4)
  3. customThe volatiles were removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-53ca40e0a0d9491fbfbd27a86937d30c
Source dataset
uspto-grants-2006_10
Patent number
US07122567B2

Reaction notes

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