Sodium borohydride → HCID 67997514, compound

HRID 1503286Notes

Reaction equation

HRID 1503286 reaction equation
C([O:3][C:4](=O)[CH:5]([NH2:29])[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:18][CH:17]=2)[CH:8]=1)C.[BH4-].[Na+]>CCO.Cl>[NH2:29][CH:5]([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:18][CH:17]=2)[CH:8]=1)[CH2:4][OH:3]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 54765934HCID 54765934, compound

Product 1

HCID 67997514HCID 67997514, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

2-Amino-3-[1-(4-phenoxyphenyl)-1H-indol-3-yl]propan-1-ol (34) was prepared as follows: A mixture of compound 33 (0.15 g, 1.0 eq) and NaBH4 (4 eq) in 15 mL of EtOH was shaken at room temperature for 72 hours. The solvent was removed under vacuum. Water (10 mL) and EtOAc (40 mL) were added to the residue. The organic layer was separated, concentrated and purified by column (Silica gel, EtOAc/MeOH/NH4OH 10/2/0.2) to get a sticky oil, which was dissolved in 25 mL of HCl (0.25N aqueous), then, freeze dried to afford compound 34 as a brown solid (45 mg, 35%): 1H-NMR (400 MHz, CD3OD) δ: 7.59 (d, 1H, 7.9 Hz), 7.4-7.44 (m, 3H), 7.28-7.32 (m, 3H), 7.04-7.15 (m, 5H), 6.95-6.99 (m, 2H), 3.7-3.74 (m, 1H), 3.47-3.58 (m, 2H), 3.01-3.12 (m, 2H); LC/MS: m/z=359.1 [M+H]+ (Calc: 358.4).

Workup

  1. custom2-Amino-3-[1-(4-phenoxyphenyl)-1H-indol-3-yl]propan-1-ol (34) was prepared
  2. customThe solvent was removed under vacuum
  3. additionWater (10 mL) and EtOAc (40 mL) were added to the residue
  4. customThe organic layer was separated
  5. concentrationconcentrated
  6. custompurified by column (Silica gel, EtOAc/MeOH/NH4OH 10/2/0.2)
  7. customto get a sticky oil, which
  8. customfreeze dried

Sources & evidence

ORD record
ord-848b4015113d4c81b0cd2d0d7a8644ca
Source dataset
uspto-grants-2015_12
Patent number
US09212139B2

Reaction notes

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