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Benzylamine → (+/-)-2-benzyl-1-(2-benzyloxy-5-fluoro-phenyl)-2,3-dihydro-1H-isoindole

HRID 2036238
Notes
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Reaction equation

HRID 2036238 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[CH:16](OS(C)(=O)=O)[C:17]1[CH:28]=[CH:27][CH:26]=[CH:25][C:18]=1[CH2:19]OS(C)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:34]([NH2:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:34]([N:41]1[CH2:19][C:18]2[C:17](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:16]1[C:10]1[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 86682589(+/-)-Methanesulfonic acid 2-[(2-benzyloxy-5-fluoro-phenyl)-methanesulfonyloxy-methyl]-benzyl ester

Product 1

HCID 86682590(+/-)-2-benzyl-1-(2-benzyloxy-5-fluoro-phenyl)-2,3-dihydro-1H-isoindole

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Conditions

Temperature
70 °C

Procedure

To a solution of (±)-methanesulfonic acid 2-[(2-benzyloxy-5-fluoro-phenyl)-methanesulfonyloxy-methyl]-benzyl ester (650 mg, 1.31 mmol, 1.0 eq.) in DMF (15 mL), benzylamine (0.19 mL, 1.71 mmol, 1.3 eq.) and DIPEA (0.69 mL, 3.94 mmol, 3.0 eq.) were added in sequence. The mixture was heated at 70° C. for 2 days. The reaction mixture was allowed to cool to r.t. and concentrated in vacuo. The residue was filtered and then purified by prep. HPLC (column: Water X-Bridge, 30×75 mm, 10 um, UV/MS, basic conditions) and concentrated in vacuo to give (±)-2-benzyl-1-(2-benzyloxy-5-fluoro-phenyl)-2,3-dihydro-1H-isoindole.

Workup

  1. temperatureto cool to r.t.
  2. concentrationconcentrated in vacuo
  3. filtrationThe residue was filtered
  4. custompurified by prep
  5. concentrationHPLC (column: Water X-Bridge, 30×75 mm, 10 um, UV/MS, basic conditions) and concentrated in vacuo

Sources & evidence

ORD record
ord-3b18df4e7c3047b7ab34190c2e2a2e9b
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08575158B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes