Sodium borohydride → HCID 54767837, compound

HRID 1503281Notes

Reaction equation

HRID 1503281 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH:5]([NH2:29])[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)[CH:14]=2)[NH:9][CH:8]=1)[CH3:2].[BH4-].[Na+]>CCO>[CH3:2][CH2:1][O:3][C:4]([CH3:5])=[O:30].[CH3:1][OH:3].[NH4+:9].[OH-:3].[NH2:29][CH:5]([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)[CH:14]=2)[NH:9][CH:8]=1)[CH2:4][OH:3]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 54767996HCID 54767996, compound

Product 2

HCID 21901312Ethyl acetate methanol ammonium hydroxideHCID 54767837HCID 54767837, compoundYield 134.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Amino-3-[5-(4-phenoxyphenyl)-1H-indol-3-yl]propan-1-ol (10) was prepared as follows: A mixture compound 7 prepared in Example 1 (0.2 g, 1.0 eq) and NaBH4 (4 eq) in 10 mL EtOH was shaken at room temperature for 72 hours. The solvent was removed under vacuum, then, water (10 mL) and EtOAc (40 mL) was added to it. The organic layer was separated, concentrated and purified by column (Silica gel, EtOAc/MeOH 10/1, then EtOAc/MeOH/NH4OH 10/2/0.2) to get compound 10 as a yellow solid (60 mg, 38%): 1H-NMR (400 MHz, CD3OD) δ: 7.76 (s, 1H), 7.6-7.65 (m, 2H), 7.32-7.46 (m, 4H), 7.16 (s, 1H), 7.02-7.12 (m, 5H), 3.74-3.78 (m, 1H), 3.55-3.6 (m, 1H), 3.4-3.46 (m, 1H), 3.06-3.12 (m, 1H), 2.96-3.02 (m, 1H); LC/MS: m/z=359.4 [M+H]+ (Calc: 358.4).

Workup

  1. custom2-Amino-3-[5-(4-phenoxyphenyl)-1H-indol-3-yl]propan-1-ol (10) was prepared
  2. customThe solvent was removed under vacuum
  3. additionwater (10 mL) and EtOAc (40 mL) was added to it
  4. customThe organic layer was separated
  5. concentrationconcentrated
  6. custompurified by column (Silica gel, EtOAc/MeOH 10/1

Sources & evidence

ORD record
ord-1343322113cf49e295ca61fdab31e492
Source dataset
uspto-grants-2015_12
Patent number
US09212139B2

Reaction notes

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