3-Fluoroacetophenone → HCID 22182428, compound

HRID 1432191Notes

Reaction equation

HRID 1432191 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[F:13][C:14]1[CH:15]=[C:16]([C:20](=O)[CH3:21])[CH:17]=[CH:18][CH:19]=1.[BH4-].[Na+]>CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[F:13][C:14]1[CH:15]=[C:16]([CH:20]([NH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10])[CH3:21])[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 99673-FluoroacetophenoneHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 4311764Sodium borohydride

Product 1

HCID 22182428HCID 22182428, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 3-aminopropylcarbamate (0.7 g, 4.05 mmol) and 1-(3-fluorophenyl)ethanone (0.5 g, 3.6 mmol) in titanium(IV) isopropoxide (1.8 mL, 6 mmol) was stirred at room temperature for 3 h. It was diluted with methanol (10 mL) and then sodium borohydride (0.22 g, 5.76 mmol) was added carefully and stirred for 10 minutes. The reaction mixture was quenched with 0.1 N NaOH (10 mL) solution. It was filtered through celite and washed with dichloromethane (2×20 mL). The organic layer was separated, dried over CaCl2 and evaporated to get the title product (1.07 g, 100%) as thick liquid. 1H NMR (400 MHz, CDCl3): δ 7.30 (m, 1H), 7.05 (m, 2H), 6.95 (m, 1H), 5.10 (bs, 1H), 3.75 (q, 1H), 3.15 (m, 2H), 2.55 (m, 1H), 2.45 (m, 1H), 1.60 (m, 2H), 1.45 (s, 9H), 1.35 (d, 3H). MS (ESI) m/z: Calculated: 296.38; Observed: 297.0 (M++1).

Workup

  1. customThe reaction mixture was quenched with 0.1 N NaOH (10 mL) solution
  2. filtrationIt was filtered through celite
  3. washwashed with dichloromethane (2×20 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over CaCl2
  6. customevaporated

Sources & evidence

ORD record
ord-7c9d7b8b2d7c40d8bccdcfd26bad13e5
Source dataset
uspto-grants-2009_11
Patent number
US07612078B2

Reaction notes

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