Sodium triacetoxyborohydride → HCID 59606132, compound

HRID 1945572Notes

Reaction equation

HRID 1945572 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][NH:13][CH3:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:15]1[CH2:18][C:17](=O)[CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.O>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][N:13]([CH3:14])[CH:17]2[CH2:16][O:15][CH2:18]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 150242543-OxetanoneHCID 46840011tert-Butyl 3-[(methylamino)methyl]azetidine-1-carboxylate

Product 1

HCID 59606132HCID 59606132, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(methylamino)methylazetidine-1-carboxylic acid tert-butyl ester (450 mg, 2.25 mmol), oxetan-3-one (135 mg, 1.88 mmol), in dichloromethane (10 mL) was stirred at RT for 1.5 h. Sodium triacetoxyborohydride (797 mg, 3.76 mmol) was added and the resulting reaction mixture was stirred at RT under nitrogen atmosphere for 18 h. The mixture was diluted with water, the phases were separated and the aqueous phase was extracted with EtOAc (2×25 mL). The combined organic layers were dried over sodium sulfate, filtered and the solvents reduced in vacuo The residue was purified by column chromatography (Si—PPC, MeOH:DCM, gradient 0:100 to 5:95) to afford the title compound as a colourless oil (330 mg, 69%). 1H NMR (400 MHz, CDCl3): δ 4.64 (2 H, t, J=6.58 Hz), 4.57 (2 H, t, J=6.26 Hz), 4.01 (2 H, t, J=8.40 Hz), 3.57-3.55 (3 H, m), 2.71-2.61 (1 H, m), 2.41 (2 H, d, J=7.57 Hz), 2.08 (3 H, s), 1.44 (9 H, s).

Workup

  1. customthe resulting reaction mixture
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with EtOAc (2×25 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. customwas purified by column chromatography (Si—PPC, MeOH:DCM, gradient 0:100 to 5:95)

Sources & evidence

ORD record
ord-6ad0cc25b0f04907bd3c1b6f73d503ee
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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