Carbamate → (Quinolin-3-yl)methanol

HRID 1260152Notes

Reaction equation

HRID 1260152 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:11](=O)([O-:13])N.[BH4-].[Na+]>C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11][OH:13])[CH:2]=1

Participants

5

Reactant 3

HCID 276Carbamate2×HCID 7047Quinoline2×HCID 4311764Sodium borohydride

Product 1

HCID 12662983(Quinolin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Synthesis of compounds ERW1041A, B, C, D, E, and 1069 were synthesized using the methods of Choi et al. Chemistry & Biology, Volume 12, Issue 4, Pages 469-475, except the amino-acid amines are protected by a quinoline-containing carbamate. This quinoline-containing carbamate is synthesized by reducing 3-quinolylcarbaldehyde with sodium borohydride in THF followed by an aqueous workup and flash chromatography yielding 3-quinolylcarbinol. para-Nitro-phenylchloroformate is reacted with 3-quinolylcarbinol in methylene chloride and N-methyl morpholine to give a carbonate of 3-quinoline methanol and para-Nitro-phenol. After purification by flash chromatography, this carbonate is reacted with the methyl ester of the amino acid in neat DMF to give the named compounds.

Workup

  1. customSynthesis of compounds ERW1041A, B, C, D, E, and 1069
  2. customwere synthesized
  3. customis synthesized

Sources & evidence

ORD record
ord-aee28e72fbe14a2ebad7ae1b3c47f3ab
Source dataset
uspto-grants-2013_06
Patent number
US08470782B2

Reaction notes

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