Sodium cyanoborohydride → Methyl 3-[N-(p-Chlorobenzyl)-3-benzyl-5-(benzoyloxy)indol-2-yl]-2,2-dimethylpropanoate

HRID 327229Notes

Reaction equation

[Cl:1][C:2]1[CH:42]=[CH:41][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][C:17](=[O:24])[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:14]=3)[C:9]([C:25](=O)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:8]2[CH2:33][C:34]([CH3:40])([CH3:39])[C:35]([O:37][CH3:38])=[O:36])=[CH:4][CH:3]=1.C([BH3-])#N.[Na+]>ClC(Cl)C.[Zn+2].[I-].[I-]>[Cl:1][C:2]1[CH:42]=[CH:41][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][C:17](=[O:24])[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:14]=3)[C:9]([CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[C:8]2[CH2:33][C:34]([CH3:40])([CH3:39])[C:35]([O:37][CH3:38])=[O:36])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

Methyl 3-[N-(p-chlorobenzyl)-3-benzoyl-5-(benzoyloxy)indol-2-yl]-2,2-dimethylpropanoate (360 mg) (prepared in Step A of Example 9), 800 mg of ZnI2, and 500 mg of sodium cyanoborohydride were stirred in 5 mL of dichloroethane at RT under argon for 30 min. The temperature was then raised to 65° C. for 3 hr. After the solution had cooled, it was poured onto 10 mL of NH4OAc (25% solution), extracted with 3×15 mL of ether, washed with 10 mL of H2O and dried (MgSO4). The solution was evaporated to dryness and the residue was chromatographed on silica gel to yield the title compound as a white foam.

Workup

temperatureAfter the solution had cooled
extractionextracted with 3×15 mL of ether
washwashed with 10 mL of H2O
dry with materialdried (MgSO4)
customThe solution was evaporated to dryness
customthe residue was chromatographed on silica gel

Sources & evidence

ORD record: ord-930a0d5ed0e54fe38ef5fccc656a694f
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05272145

Reaction notes

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