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Methanol → (R)-tert-butyl 3-amino-3-(3-fluoro-4-(trifluoromethyl)phenyl)propylcarbamate

HRID 2279535
Notes
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Reaction equation

HRID 2279535 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[C@@H:12]([C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[C:25]([F:33])[CH:24]=1)[CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].CO.C1COCC1.O.NN>O>[NH2:3][C@@H:12]([C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:30])([F:31])[F:32])=[C:25]([F:33])[CH:24]=1)[CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:19])[CH3:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 68294223(R)-tert-butyl 3-(1,3-dioxoisoindolin-2-yl)-3-(3-fluoro-4-(trifluoromethyl)phenyl)propylcarbamate

Product 1

HCID 86705529(R)-tert-butyl 3-amino-3-(3-fluoro-4-(trifluoromethyl)phenyl)propylcarbamateYield 59.5%

Reagents, catalysts & solvents

1
HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 288 (0.350 g, 0.750 mmol) and MeOH:THF (6 mL, 1:1) was added hydrazine monohydrate (0.188 mL, 3.75 mmol) and the reaction was heated to 50° C. for 4 d. The reaction was then poured into water, and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (500:20) to afford 0.150 g (59.4%) of (R)-tert-butyl 3-amino-3-(3-fluoro-4-(trifluoromethyl)phenyl)propylcarbamate (290).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by SiO2 chromatography
  6. washeluting with DCM/MeOH (500:20)

Sources & evidence

ORD record
ord-ce09d9c392504c45bb5e23f0e05a1984
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09133187B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes