Hydrochloric Acid → HCID 178445713, compound

HRID 2404109Notes

Reaction equation

HRID 2404109 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH:18]3[CH2:23][CH2:22][CH:21]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:20][CH2:19]3)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>C1COCC1>[C:24]([C@H:21]1[CH2:22][CH2:23][C@H:18]([O:17][C:13]2[CH:12]=[C:11]3[C:16](=[CH:15][CH:14]=2)[NH:8][CH2:9][CH2:10]3)[CH2:19][CH2:20]1)([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66926375HCID 66926375, compound

Product 1

HCID 178445713HCID 178445713, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(4-tert-butyl-cyclohexyloxy)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (0.92 g, 2.5 mmol) in THF (10 mL) was added 4 M HCl in dioxane (6 mL, 25 mmol). The mixture was stirred at room temperature for 48 hrs to form white precipitate. This mixture was partitioned between dichloromethane and aqueous sodium bicarbonate, and the organic phase was dried over MgSO4, filtered and concentrated. The crude was purified with a silica gel column eluted with methanol in dichloromethane from 0 to 8% to give precipitate (0.67 g, yield: 99%). ESI-MS: 274.2 (M+H)+.

Workup

  1. customto form white precipitate
  2. customThis mixture was partitioned between dichloromethane and aqueous sodium bicarbonate
  3. dry with materialthe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was purified with a silica gel column
  7. washeluted with methanol in dichloromethane from 0 to 8%

Sources & evidence

ORD record
ord-1d925c09c95a4d87b66e5c44a52a7bb6
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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