Methoxyacetic Acid → HCID 69919575, compound

HRID 2307471Notes

Reaction equation

HRID 2307471 reaction equation
[C:1]1([CH:7]=[CH:8][C:9]([NH:11][CH:12]([C:14]2[CH:23]=[C:22]3[C:17]([CH2:18][CH2:19][CH2:20][NH:21]3)=[CH:16][CH:15]=2)[CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].[CH3:26][O:27][CH2:28][C:29](O)=O>>[CH3:26][O:27][CH2:28][CH2:29][N:21]1[C:22]2[C:17](=[CH:16][CH:15]=[C:14]([CH:12]([NH:11][C:9](=[O:10])[CH:8]=[CH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH3:13])[CH:23]=2)[CH2:18][CH2:19][CH2:20]1

Participants

4

Reactant 3

HCID 12251Methoxyacetic AcidHCID 4311764Sodium borohydrideHCID 69850326HCID 69850326, compound

Product 1

HCID 69919575HCID 69919575, compoundYield 66%

Conditions

Temperature
23 °C

Procedure

To a stirred solution of 3-phenyl-N-[1-(1,2,3,4-tetrahydro-quinolin-7-yl)ethyl]acrylamide (Example 233) (75 mg, 0.245 mmol) in methoxyacetic acid (5 ml) was added, in small portions, NaBH4 (232 mg) over 30 minutes. The mixture was stirred at 23° C. for an additional 2 hours and then the excess hydride destroyed by adding MeOH. That solution was diluted with EtOAc and washed several times with water. The organic phase was dried (MgSO4) and evaporated. The crude material was purified by chromatography (SiO2, 25% EtOAc in hexane) yielding 59 mg (66%) of the desired compound as a thick oil.

Workup

  1. customthe excess hydride destroyed
  2. additionby adding MeOH
  3. additionThat solution was diluted with EtOAc
  4. washwashed several times with water
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customevaporated
  7. customThe crude material was purified by chromatography (SiO2, 25% EtOAc in hexane)

Sources & evidence

ORD record
ord-ede1a26a4fa249c78796e6a141fc83f0
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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