Lithium borohydride → HCID 53969787, compound

HRID 1200058Notes

Reaction equation

HRID 1200058 reaction equation
[C:1]([NH:4][CH:5]([CH:11]([C:13]1[S:14][C:15]([CH:18]=[CH:19][C:20]2[C:21]3[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=3[S:23][CH:24]=2)=[CH:16][CH:17]=1)[OH:12])[C:6](OCC)=[O:7])(=[O:3])[CH3:2].[BH4-].[Li+]>O1CCCC1>[S:23]1[CH:24]=[C:20]([CH:19]=[CH:18][C:15]2[S:14][C:13]([CH:11]([OH:12])[CH:5]([NH:4][C:1](=[O:3])[CH3:2])[CH2:6][OH:7])=[CH:17][CH:16]=2)[C:21]2[CH:28]=[CH:27][CH:26]=[CH:25][C:22]1=2

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 54450364HCID 54450364, compound

Product 1

HCID 53969787HCID 53969787, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred, chilled (-5° C.) suspension of ethyl 2-acetamido-3-[5-[2-(benzo[b]-thiophen-3-yl)ethenyl]thiophen-2-yl]-3-hydroxypropionate (4.0 g) and tetrahydrofuran (40 ml) was treated with lithium borohydride (5.8 ml of a 2.0M solution in tetrahydrofuran) over 3 mins. After stirring overnight at ambient temperature, the mixture was sequentially quenched with methanol (5 ml), water (20 ml), and 10% hydrochloric acid (5 ml). The organic solvent was removed in vacuo, and the aqueous phase was basified with 10% sodium hydroxide solution and extracted with dichloromethane and ether. The combined dried over anhydrous sodium sulfate organic phase was filtered and evaporated. The residue was purified by high performance liquid chromatography (silica gel, sample loaded in dichloromethane, eluted with 10% methanol in dichloromethane). The appropriate fractions were combined and evaporated to yield 2.23 g (62%) of product, mp 144°-145° C.

Workup

  1. temperatureA stirred, chilled
  2. customthe mixture was sequentially quenched with methanol (5 ml), water (20 ml), and 10% hydrochloric acid (5 ml)
  3. customThe organic solvent was removed in vacuo
  4. extractionextracted with dichloromethane and ether
  5. dry with materialThe combined dried over anhydrous sodium sulfate organic phase
  6. filtrationwas filtered
  7. customevaporated
  8. customThe residue was purified by high performance liquid chromatography (silica gel, sample loaded in dichloromethane, eluted with 10% methanol in dichloromethane)
  9. customevaporated

Sources & evidence

ORD record
ord-f8a91baf50ff47f09920cf83ef98c21d
Source dataset
uspto-grants-1990_02
Patent number
US04904674

Reaction notes

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