Methylamine → HCID 52912223, compound

HRID 2366905Notes

Reaction equation

HRID 2366905 reaction equation
[CH3:1][CH:2]([O:4][C:5](=[O:29])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]=O)=[CH:19][CH:18]=3)[CH:15]=2)[N:10]([C:25](=[O:27])[CH3:26])[C@@H:9]([CH3:28])[CH2:8]1)[CH3:3].[CH3:30][NH2:31].C1COCC1.[BH4-].[Na+]>CO>[CH3:3][CH:2]([O:4][C:5](=[O:29])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]([CH2:23][NH:31][CH3:30])=[CH:21][CH:22]=3)[CH:15]=2)[N:10]([C:25](=[O:27])[CH3:26])[C@@H:9]([CH3:28])[CH2:8]1)[CH3:1]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 86669228HCID 86669228, compound

Product 1

HCID 52912223HCID 52912223, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Methylethyl[(2S,4R)-1-acetyl-6-(4-formylphenyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 36) (100 mg, 0.254 mmol) was dissolved in methanol (3 mL) and 2M methylamine in THF (0.254 mL, 0.507 mmol) was added. The yellow solution was stirred under nitrogen at room temperature for 135 minutes at which point sodium borohydride (15.35 mg, 0.406 mmol) was added. The reaction was stirred for 1 h then left sitting overnight. The reaction was quenched with sat. aqueous sodium bicarbonate solution (1 mL) and EtOAc (8 mL) was added. A white solid was filtered off (bond elut reservoir) and found to be the desired product (34 mg). The filtrate was partitioned and the organic layer dried. Concentration of the organic layer gave 67 mg of a colourless residue which was applied to a silica 12+S Biotage column and purified eluting with a gradient of 1-5% methanolic ammonia in DCM. Concentration of the product containing fractions gave another batch of the desired product (52 mg).

Workup

  1. additionwas added
  2. waitthen left
  3. waitsitting overnight
  4. customThe reaction was quenched with sat. aqueous sodium bicarbonate solution (1 mL) and EtOAc (8 mL)
  5. additionwas added
  6. filtrationA white solid was filtered off (bond elut reservoir)
  7. customThe filtrate was partitioned
  8. customthe organic layer dried

Sources & evidence

ORD record
ord-238980f94db545d7b1d55edc797cb96c
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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