Tert-Butylamine → HCID 89422900, compound

HRID 1481743Notes

Reaction equation

HRID 1481743 reaction equation
[Si:1]([O:8][CH:9]1[C:13]2=[CH:14][C:15]3[CH:16]=[C:17]([C:21](=O)[CH2:22][CH2:23][CH3:24])[CH:18]=[CH:19][C:20]=3[N:12]2[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:26]([NH2:30])([CH3:29])([CH3:28])[CH3:27]>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[Si:1]([O:8][CH:9]1[C:13]2=[CH:14][C:15]3[CH:16]=[C:17]([C:21](=[N:30][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:22][CH2:23][CH3:24])[CH:18]=[CH:19][C:20]=3[N:12]2[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6385Tert-ButylamineHCID 71284529HCID 71284529, compound

Product 1

HCID 89422900HCID 89422900, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(1-(tert-butyldimethylsilyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)butan-1-one (3.2 g, 9.0 mmol), prepared according to procedure described in Example 151 Step 5, in CH2Cl2 (40 mL), cooled to 0° C., was added tBuNH2 (3.0 mL, 27.0 mmol). To this mixture was added a solution of TiCl4 (5.4 mL, 1M, 5.4 mmol) in CH2Cl2 dropwise via an addition funnel. Upon completion of addition, the reaction was stirred at room temperature for 24 hrs before it was quenched with a saturated solution of NaHCO3. The aqueous phase was extracted with CH2Cl2 and the combined organic phases were dried over Na2SO4, filtered, and concentrated to give a crude product that was used immediately without further purification. LC-MS 413.5 [M+H]+, RT 0.98 min.

Workup

  1. additionUpon completion of addition
  2. customwas quenched with a saturated solution of NaHCO3
  3. extractionThe aqueous phase was extracted with CH2Cl2
  4. dry with materialthe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-de284eec47c14303b64a2a82b715b191
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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