Sodium triacetoxyborohydride → HCID 68292986, compound

HRID 2276918Notes

Reaction equation

HRID 2276918 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@@H:2]1[C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.Cl.[CH3:20][O:21][C:22]([CH:24]1[CH2:29][CH2:28][N:27](C)[CH2:26][CH2:25]1)=[O:23].[C:31](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.C([O-])(O)=O.[Na+]>[CH3:20][O:21][C:22]([C:24]1([CH3:31])[CH2:25][CH2:26][N:27]([CH2:15][C:14]2[CH:17]=[CH:18][C:11]([C@@H:2]3[O:1][C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=4[O:4][CH2:3]3)=[CH:12][CH:13]=2)[CH2:28][CH2:29]1)=[O:23]

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 68593680HCID 68593680, compoundHCID 86691113HCID 86691113, compound

Product 1

HCID 68292986HCID 68292986, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Intermediate A (100 mg, 0.42 mmol), methyl-piperidine-4-carboxylic acid methyl ester hydrochloride (105 mg, 0.54 mmol), and TEA (75 uL, 0.54 mmol) are stirred in dry THF (3 mL) for 10 minutes. Sodium triacetoxyborohydride (176 mg) is added and stirred for 4 h. The mixture is diluted with saturated NaHCO3 and extracted with EtOAc. The organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated. The residue is purified by flash chromatography eluting with a gradient of 0-3% MeOH in DCM to give [(S)-4-(2,3-dihydro-benzo[1,4]dioxin-2-yl)-benzyl]-4-methyl-piperidine-4-carboxylic acid methyl ester.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer is washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography
  7. washeluting with a gradient of 0-3% MeOH in DCM

Sources & evidence

ORD record
ord-94881275ed984a45ba8eb0bdc18992e9
Source dataset
uspto-grants-2015_09
Patent number
US09133146B2

Reaction notes

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