Methylamine → HCID 69362737, compound

HRID 723753Notes

Reaction equation

HRID 723753 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:24]=[CH:23][N:22]=[N:21]4)[O:16][C:15]3=[O:25])=[CH:10][C:9]=2[F:26])[CH2:4][CH2:3]1.CN.C(O[BH3-])(=O)C.[Na+].[CH2:35]([N:37](CC)CC)C>O1CCCC1.ClCCl.C(O)(=O)C.O>[CH3:35][NH:37][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:24]=[CH:23][N:22]=[N:21]4)[O:16][C:15]3=[O:25])=[CH:10][C:9]=2[F:26])[CH2:4][CH2:3]1

Participants

9

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 23670382SodiumacetoxyborohydrideHCID 69364625HCID 69364625, compound

Product 1

HCID 69362737HCID 69362737, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

(5R)-3-(4-(4-Oxopiperidin-1-yl)-3-fluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one (250 mg, 0.70 mM) was dissolved in a mixture of anhydrous tetrahydrofuran (5 ml) and dichloromethane (5 ml) under nitrogen. Acetic acid (1 drop), methylamine (33% solution in methanol, 31 μL, 0.77 mM) and sodium acetoxyborohydride (222 mg, 1.05 mM) were added, and the mixture stirred at ambient temperature for 3 hours. The mixture was diluted with water (15 ml) and dichloromethane (15 ml), and the pH adjusted to 9 by addition of triethylamine. The organic phase was separated, washed with water (2×15 ml), brine (15 ml), and dried (magnesium sulfate). Evaporation gave the desired product (145 mg).

Workup

  1. customThe organic phase was separated
  2. washwashed with water (2×15 ml), brine (15 ml)
  3. dry with materialdried (magnesium sulfate)
  4. customEvaporation

Sources & evidence

ORD record
ord-f7dcd40c790144fa815a314ba21cc97d
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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