Acetic Acid → 1-(8-fluoro-1,2,3,4-tetrahydrodibenzo[b,d]furan-2-yl)-N-{[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl]methanamine

HRID 1593649Notes

Reaction equation

HRID 1593649 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]3[CH2:10][CH2:11][CH:12]([CH:14]=O)[CH2:13][C:7]=3[C:6]=2[CH:16]=1.[CH3:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]3[O:31][CH2:30][C@H:29]([CH2:32][NH2:33])[O:28][C:24]3=2)[N:19]=1.[BH3-]C#N.[Na+].CC(O)=O>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]3[CH2:10][CH2:11][CH:12]([CH2:14][NH:33][CH2:32][C@@H:29]4[O:28][C:24]5=[C:25]6[C:20](=[CH:21][CH:22]=[C:23]5[O:31][CH2:30]4)[N:19]=[C:18]([CH3:17])[CH:27]=[CH:26]6)[CH2:13][C:7]=3[C:6]=2[CH:16]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 23521566[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methylamineHCID 866076498-Fluoro-1,2,3,4-tetrahydrodibenzo[b,d]furan-2-carbaldehyde

Product 1

HCID 692356891-(8-fluoro-1,2,3,4-tetrahydrodibenzo[b,d]furan-2-yl)-N-{[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl]methanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8-fluoro-1,2,3,4-tetrahydrodibenzo[b,d]furan-2-carbaldehyde (0.040 g, 0.18 mmol), [(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methylamine (0.042 g, 0.18 mmol), and NaBH3CN (0.023 g, 0.38 mmol) were stirred together in MeOH (1.2 mL) under a N2 atmosphere. To this mixture was added AcOH (0.023 mL) and reaction was allowed to stir for 3 h. The reaction mixture was concentrated and the resulting oil was purified by flash chromatography on silica gel to afford title compound as a mixture of two diastereomers (0.068 g, 88%). The diastereomers were separated by HPLC on a Chiracel AD column (2×25 cm), eluting with 100% ethanol; MS (ES) m/z=433.1 [M+H]+.

Workup

  1. additionTo this mixture was added
  2. concentrationThe reaction mixture was concentrated
  3. customthe resulting oil was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-c673d927c2aa4e0fb9dd2c0ae99c5866
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

Loading…