Acetic Acid → HCID 20197302, compound

HRID 1904766Notes

Reaction equation

HRID 1904766 reaction equation
[C:1]1([CH2:7][O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:23](O)=[O:24])[CH:21]=3)[NH:16][CH:15]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[BH4-].[Li+].C(O)(=O)C>O1CCCC1>[OH:24][CH2:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:13][CH2:12][NH:11][C:9](=[O:10])[O:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 4148881Lithium borohydrideHCID 14326577HCID 14326577, compound

Product 1

HCID 20197302HCID 20197302, compoundYield 104.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-[2-[[(phenylmethoxy)carbonyl]amino]ethyl]-1H-indole-5-carboxylic acid (9 g) and carbonyldiimidazole (5.2 g) in dry tetrahydrofuran (THF) (150 ml) was stirred vigorously under nitrogen at room temperature for 5 h. A solution of lithium borohydride (1.6 g) in dry THF (70 ml) was added over 70 min and the mixture then stirred for 18 h. Aqueous acetic acid (30%, 25 ml) was added slowly to the ice-cooled mixture and the solution was then partitioned between brine (25%, 300 ml) and ethyl acetate (250 ml). The organic layer was washed with sulphuric acid (0.4M, saturated with sodium chloride, 3×80 ml), brine (100 ml) and potassium carbonate solution (25%, 2×100 ml). The dried (MgSO4) solution was evaporated in vacuo, the residue taken up in dichloromethane (150 ml) and insoluble material was filtered off. The filtrate was evaporated in vacuo to leave the alcohol (9 g) as a colourless oil containing some (ca. 45 mole %) ethyl acetate. T.l.c. Si02 /Et2O, Rf 0.25.

Workup

  1. temperaturecooled mixture
  2. customthe solution was then partitioned between brine (25%, 300 ml) and ethyl acetate (250 ml)
  3. washThe organic layer was washed with sulphuric acid (0.4M, saturated with sodium chloride, 3×80 ml), brine (100 ml) and potassium carbonate solution (25%, 2×100 ml)
  4. dry with materialThe dried (MgSO4) solution
  5. customwas evaporated in vacuo
  6. filtrationinsoluble material was filtered off
  7. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-c11e1ec54b8b4d6a90bea9e5129764c0
Source dataset
uspto-grants-1989_06
Patent number
US04839377

Reaction notes

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