Sodium borohydride → 3-{4-[2-(4-tert-Butoxycarbonylaminophenyl)ethoxy]phenyl}-2-ethoxypropanol

HRID 987122Notes

Reaction equation

HRID 987122 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([O:31][CH2:32][CH3:33])[C:26](OCC)=[O:27])=[CH:20][CH:19]=2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([O:31][CH2:32][CH3:33])[CH2:26][OH:27])=[CH:20][CH:19]=2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22988408Ethyl 3-(4-[2-(4-tert-butoxycarbonylaminophenyl)ethoxy]phenyl}-2-ethoxypropanoate

Product 1

HCID 229884173-{4-[2-(4-tert-Butoxycarbonylaminophenyl)ethoxy]phenyl}-2-ethoxypropanolYield 55.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The compound was synthesised in an analogous method to Example 1 using ethyl 3-{4-[2-(4-tert-butoxycarbonylaminophenyl)ethoxy]phenyl)-2-ethoxypropanoate (0.994 g, 2.172 mmol) and sodium borohydride (0.164 g, 4.34 mmol). The reaction was quenched after 21 hours and the product was extracted with ethyl acetate. The organic phase was washed with sodium sulfite and brine, dried (sodium sulfate), filtered and solvent was evaporated in vacuo. The crude product was purified by chromatography on silica gel using heptane:ethyl acetate (gradient 2:1 tol:2) as eluants to give 0.5 g (yield 55%) of the desired product.

Workup

  1. customThe reaction was quenched after 21 hours
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic phase was washed with sodium sulfite and brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customsolvent was evaporated in vacuo
  7. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c01c5b61f3834977b0cfbe71e30cd292
Source dataset
uspto-grants-2003_10
Patent number
US06630509B2

Reaction notes

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