Ammonium Acetate → Tert-butyl 2-amino-2-(3-fluorophenyl)ethylcarbamate

HRID 339959Notes

Reaction equation

HRID 339959 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1)=O)([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:25].[Na+]>CO>[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][CH:9]([NH2:25])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 84173790tert-butyl N-[2-(3-fluorophenyl)-2-oxoethyl]carbamate

Product 1

HCID 76853774Tert-butyl 2-amino-2-(3-fluorophenyl)ethylcarbamateYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a flask were added tert-butyl[2-(3-fluorophenyl)-2-oxoethyl]carbamate (0.32 g, 1.3 mmol) and ammonium acetate (2.02 g, 26.2 mmol) and methanol (10 mL) and sodium cyanoborohydride (0.22 g, 3.5 mmol). The mixture was refluxed for 2 h. The solvent was removed under vacuum. To the residue was added EtOAc and 50 mL of 1M NaOH. The aqueous phase was extracted again with fresh EtOAc. The combined organic extracts were dried over sodium sulfate, filtered and dried under vacuum to give 0.301 g (94% yield) of the final product as oil. LC-MS found: 155.1 (M−Boc)+.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customThe solvent was removed under vacuum
  3. additionTo the residue was added EtOAc and 50 mL of 1M NaOH
  4. extractionThe aqueous phase was extracted again with fresh EtOAc
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-ea277ebecd2a4704bf0fe33706cb0ab8
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

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