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

HRID 1417968Notes

Reaction equation

[BH4-].[Na+].[CH2:3]([O:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[C:13]1[C:36]([CH2:37][O:38][CH3:39])=[C:35]([CH:40]=[O:41])[N:34]=[CH:33][C:14]=1[N:15]2[CH2:20][C:21]([N:23]([CH3:32])[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCCC1>[CH2:3]([O:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[C:13]1[C:36]([CH2:37][O:38][CH3:39])=[C:35]([CH2:40][OH:41])[N:34]=[CH:33][C:14]=1[N:15]2[CH2:20][C:21]([N:23]([CH3:32])[CH2:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:22])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

25 mg of sodium borohydride is added to a solution of 35 mg of 5-benzyloxy-4-methoxymethyl-9-{2-[N-methyl-N-(2-phenylethyl)-amino]-2-oxoethyl}-9H-pyrido[3,4-b]indole-3-carbaldehyde in 1 ml of tetrahydrofuran at 0° C., and it is then stirred for 3 hours at 0° C. Then, the reaction mixture is poured into ice water and extracted three times with ethyl acetate. The organic phase is dried on magnesium sulfate, filtered and concentrated by evaporation in a vacuum. 34 mg of 5-benzyloxy-3-hydroxymethyl-4-methoxymethyl-9-{2-[N-methyl-N-(2-phenylethyl)-amino]-2-oxoethyl}-9H-pyrido[3,4-b]indole is obtained.

Workup

extractionextracted three times with ethyl acetate
customThe organic phase is dried on magnesium sulfate
filtrationfiltered
concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record: ord-35b9fc0bf2f94967b769064e45784d78
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05880126

Reaction notes

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