Carbamate → (Quinolin-3-yl)methanol

HRID 1689618Notes

Reaction equation

HRID 1689618 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 ERW1041 A, 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 ERW1041 A, B, C, D, E, and 1069
  2. customwere synthesized
  3. customis synthesized

Sources & evidence

ORD record
ord-abbecdd4d3944bdba75c3be8ce3b9237
Source dataset
uspto-grants-2012_04
Patent number
US08153593B2

Reaction notes

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