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2,4-Dimethoxybenzylamine → (2S)-1-(9H-carbazol-4-yloxy)-3-[(2,4-dimethoxybenzyl)amino]propan-2-ol

HRID 507335
Notes
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Reaction equation

HRID 507335 reaction equation
[O:1]1[CH2:18][C@H:2]1[CH2:3][O:4][C:5]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.[CH3:19][O:20][C:21]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:22]=1[CH2:23][NH2:24]>CCOC(C)=O.CC(O)C>[CH:8]1[C:9]2[NH:10][C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]=2[C:5]([O:4][CH2:3][C@@H:2]([OH:1])[CH2:18][NH:24][CH2:23][C:22]2[CH:25]=[CH:26][C:27]([O:29][CH3:30])=[CH:28][C:21]=2[O:20][CH3:19])=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 10879208(S)-(+)-4-(2,3-Epoxypropoxy)carbazole

Product 1

HCID 16045052(2S)-1-(9H-carbazol-4-yloxy)-3-[(2,4-dimethoxybenzyl)amino]propan-2-olYield 48%

Reagents, catalysts & solvents 1

HCID 22055037Isopropanol ethyl acetateSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of (S)-(+)-4-(2,3-Epoxypropoxy)-carbazole (7.56 g, 0.031 mole) in EtOAc/IPA (40/80 mL) was added 2,4-dimethoxybenzylamine (9.48 mL, 0.063 mole) and the reaction mixture was slowly heated to 80-90° C. and then refluxed for 5 hours. Subsequently the reaction mixture was cooled to room temperature and purified following the procedure similar to one described in step 11 for the synthesis of example 23, to afford the desired compound as colorless solid (6 g, 48%) with m.p: 152-154° C. 1H NMR (400 MHz, CDCl3): δ 2.17 (s 1H), 2.88-2.92 (m, 1H), 2.98-3.00 (m, 1H), 3.74-3.87 (m, 8H), 4.18-4.32 (m, 3H), 6.38-6.45 (m, 2H), 6.67 (d, 1H, J=8.0 Hz), 7.05 (d, 1H, J=8.0 Hz), 7.12 (d, 1H, J=8.0 Hz), 7.18-7.40 (m, 4H), 8.08 (s, 1H), 8.21 (d, 1H, J=8.0 Hz). MS m/z: 407.1 (M+1). Chiral purity: 99.96%

Workup

  1. temperaturerefluxed for 5 hours
  2. temperatureSubsequently the reaction mixture was cooled to room temperature
  3. custompurified
  4. customdescribed in step 11 for the synthesis of example 23

Sources & evidence

ORD record
ord-d800dee02b404e4d907ee9ae4cca8a8a
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07786142B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes