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4-Fluorobenzylamine → HCID 68432621, compound

HRID 1162844
Notes
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Reaction equation

HRID 1162844 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C1COCC1>[CH2:1]([O:8][CH2:9][CH:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:11][NH:27][CH2:26][C:25]1[CH:28]=[CH:29][C:22]([F:21])=[CH:23][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 673264-FluorobenzylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 14523252HCID 14523252, compound

Product 1

HCID 68432621HCID 68432621, compound

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a stirred solution of tert-butyl 2-(benzyloxy)-1-formylethylcarbamate (3.29 g, 11.8 mmol) in anhydrous THF (12 mL) was added 4-fluorobenzylamine (2.03 mL, 17.7 mmol). After 10 min, sodium triacetoxyborohydride (3.99 g, 18.8 mmol) was added, and the reaction was stirred at ambient temperature under inert atmosphere for 30 min. Saturated aqueous NaHCO3 solution was added and the mixture stirred until gas evolution ceased. The aqueous layer was extracted with EtOAc, saturated with NaCl and again extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo. The resulting cloudy yellow oil was purified by silica gel chromatography (EtOAc to 10% MeOH/EtOAc) to afford the title compound as a pale yellow oil. 1H NMR (500 MHz, CDCl3) δ 7.37-7.23 (m, 7H), 7.03-6.96 (m, 2H), 5.04 (br s, 1H), 4.49 (dd, J=11.5, 18.0 Hz, 2H), 3.86 (br s, 1H), 3.76-3.70 (m, 2H), 3.60 (dd, J=3.0, 9.0 Hz, 1H), 3.53 (d, J=4.5 Hz, 1H), 2.83-2.80 (m, 1H), 2.76-2.72 (m, 1H), 1.44 (s, 9H). ES MS (M+1)=389.5.

Workup

  1. stirringthe mixture stirred until gas evolution
  2. extractionThe aqueous layer was extracted with EtOAc, saturated with NaCl
  3. extractionagain extracted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting cloudy yellow oil was purified by silica gel chromatography (EtOAc to 10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-10b575656c084260a621688aefe929fe
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07820680B2

Reaction notes

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