Water → 5-benzyloxy-4-methoxymethyl-9-{2-[N-methyl-N-(2-phenylethyl)-amino]-2-oxoethyl}-9H-pyrido[3,4-b]indole-3-carbaldehyde

HRID 1417967Notes

Reaction equation

CC([O:4][C:5]([C:7]1[N:40]=[CH:39][C:10]2[N:11]([CH2:26][C:27]([N:29]([CH3:38])[CH2:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:28])[C:12]3[C:17]([C:9]=2[C:8]=1[CH2:41][O:42][CH3:43])=[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:15]=[CH:14][CH:13]=3)=O)C.[H-].C([Al+]CC(C)C)C(C)C.C(O)(C)C.O>O1CCCC1.C1(C)C=CC=CC=1>[CH2:19]([O:18][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:17]=1[C:9]1[C:8]([CH2:41][O:42][CH3:43])=[C:7]([CH:5]=[O:4])[N:40]=[CH:39][C:10]=1[N:11]2[CH2:26][C:27]([N:29]([CH3:38])[CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

200 mg of 5-benzyloxy-4-methoxymethyl-9-{2-[N-methyl-N-(2-phenylethyl)-amino]-2-oxoethyl}-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester is dissolved in 3 ml of tetrahydrofuran. Then, 0.29 ml of a 1.2 molar solution of diisobutylaluminum hydride in toluene is added in drops to the solution at 0° C., and it is stirred for 30 minutes at 0° C. Then, the reaction mixture is mixed with 0.1 ml of isopropanol and then with 0.1 ml of water, it is stirred for 2 hours at room temperature, filtered, and the filtrate is concentrated by evaporation in a vacuum. The residue is recrystallized from ethyl acetate, and 43 mg of 5-benzyloxy-4-methoxymethyl-9-{2-[N-methyl-N-(2-phenylethyl)-amino]-2-oxoethyl}-9H-pyrido[3,4-b]indole-3-carbaldehyde is obtained as colorless crystals with a melting point of 192°-197° C.

Workup

filtrationfiltered
concentrationthe filtrate is concentrated by evaporation in a vacuum
customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-15c18cef61fd457e83bb5808ae63b5d2
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05880126

Reaction notes

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