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Sodium borohydride → 5-(hydroxymethyl)-N-[4-(propylcarbamoyl)phenyl]-1,3-dihydro-2H-isoindole-2-carboxamide

HRID 624114
Notes
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Reaction equation

HRID 624114 reaction equation
[Cl-].[Ca+2].[Cl-].[CH2:4]([NH:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([N:19]2[CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:28](OC)=[O:29])[CH:25]=3)[CH2:20]2)=[O:18])=[CH:12][CH:11]=1)=[O:9])[CH2:5][CH3:6].[BH4-].[Na+]>C(O)C.O1CCCC1>[OH:29][CH2:28][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][CH:23]=1)[CH2:20][N:19]([C:17]([NH:16][C:13]1[CH:14]=[CH:15][C:10]([C:8](=[O:9])[NH:7][CH2:4][CH2:5][CH3:6])=[CH:11][CH:12]=1)=[O:18])[CH2:27]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 57509896Methyl 2-(4-(propylcarbamoyl)phenylcarbamoyl)isoindoline-5-carboxylate

Product 1

HCID 575098995-(hydroxymethyl)-N-[4-(propylcarbamoyl)phenyl]-1,3-dihydro-2H-isoindole-2-carboxamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent
HCID 8028
Tetrahydrofuran
Solvent

Procedure

A solution of calcium chloride (0.031 g, 0.277 mmol) in ethanol (0.8 mL) was added to a suspension of methyl 2-(4-(propylcarbamoyl)phenylcarbamoyl)isoindoline-5-carboxylate (0.04 g, 0.105 mmol) in tetrahydrofuran (1 mL). Sodium borohydride (0.02 g, 0.524 mmol) was then added in one portion and the suspension stirred at room temperature. After 18 hours, the mixture was concentrated to remove tetrahydrofuran then saturated aqueous sodium bicarbonate and water was added. The suspension was filtered and the solid was flash chromatographed to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.55 (s, 1H), 8.25 (t, J=5.6 Hz, 1H), 7.74-7.78 (m, 2H), 7.64-7.67 (m, 2H), 7.31 (d, J=4.0 Hz, 1H), 7.30 (d, J=2.3 Hz, 1H), 7.26 (d, J=8.0 Hz, 1H), 5.19 (t, J=5.6 Hz, 1H), 4.71-4.78 (m, 4H), 4.52 (d, J=5.4 Hz, 2H), 3.15-3.25 (m, 2H), 1.46-1.59 (m, 2H), 0.89 (t, J=7.4 Hz, 3H); MS (ESI(+)) m/e 354 (M+H)+.

Workup

  1. concentrationthe mixture was concentrated
  2. customto remove tetrahydrofuran
  3. additionsaturated aqueous sodium bicarbonate and water was added
  4. filtrationThe suspension was filtered
  5. customchromatographed

Sources & evidence

ORD record
ord-4b6585854be04b9f9f01941a411933f4
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09302989B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes