9-(2-Benzyloxy-ethyl)-2-methyl-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid diethylamide → 9-(2-Hydroxy-ethyl)-2-methyl-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid diethylamide
Reaction equation
[CH2:1]([N:3]([CH2:30][CH3:31])[C:4]([CH:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:19][CH2:20][O:21]CC3C=CC=CC=3)[C:10]=2[CH2:9][CH:8]([CH3:29])[CH2:7]1)=[O:5])[CH3:2]>CO.[Pd]>[CH2:30]([N:3]([CH2:1][CH3:2])[C:4]([CH:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:19][CH2:20][OH:21])[C:10]=2[CH2:9][CH:8]([CH3:29])[CH2:7]1)=[O:5])[CH3:31]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 9-(2-benzyloxy-ethyl)-2-methyl-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid diethylamide (48) (460 mg, 1.1 mmol) in methanol (25 mL) was added a slurry of Pd/C (100 mg) in methanol (5 mL). The mixture was placed on the Parr hydrogenator and shaken for 24 h under a hydrogen atmosphere. The reaction was filtered through a pad of celite, washed with methanol and concentrated in vacuo to afford 250 mg (79%) of 9-(2-hydroxy-ethyl)-2-methyl-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid diethylamide (49) as a yellow oil which was used in the next step without purification. The structure was confirmed by 1H NMR (300 MHz, CDCl3) δH 1.20-1.40 (9H, m, CH3 and N(CH2CH3)2), 1.90-2.20 (3H, m, 2-CH and 3-CH2), 2.35-2.45 (1H, m, 1-CH2), 2.85-2.95 (1H, m, 1-CH2), 3.40-3.70 (4H, m, N(CH2CH3)2), 3.70-3.80 (1H, m, 4-CH), 4.10-4.30 (4H, m, NCH2CH2OH), 6.91 (1H, t, J=7 Hz, NCCHCHCHCH), 7.00 (1H, t, J=7 Hz, NCCHCHCHCH), 7.12 (1H, d, J=7 Hz, NCCHCHCHCH), and 7.15 (1H, d, J=7 Hz, NCCHCHCHCH).
Workup
- filtrationThe reaction was filtered through a pad of celite
- washwashed with methanol
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-5361a28c36e94bfc8147a547698aee78
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09220795B2
Reaction notes
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