Sodium triacetoxyborohydride → HCID 59606201, compound

HRID 1945507Notes

Reaction equation

HRID 1945507 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH3:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:16]1[CH2:19][C:18](=O)[CH2:17]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([CH3:15])[CH:18]2[CH2:17][O:16][CH2:19]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 150242543-OxetanoneHCID 15380702tert-Butyl 4-(methylamino)piperidine-1-carboxylate

Product 1

HCID 59606201HCID 59606201, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4-(methylamino)piperidine-1-carboxylic acid tert-butyl ester (200 mg, 0.93 mmol) and oxetan-3-one (56 mg, 0.78 mmol) in DCE (6 mL) was stirred at room temperature for 2 h before the addition of sodium triacetoxyborohydride (264 mg, 1.24 mmol). The resulting mixture was stirred for 16 h, then loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH/DCM and the product eluted with 2M NH3/MeOH. The resulting oil was purified by column chromatography (Si—PCC, MeOH/DCM, 0-20%) affording 4-(Methyl(oxetan-3-yl)amino)piperidine-1-carboxylic acid tert-butyl ester as an oil (40 mg, 16%). 1H NMR (CDCl3, 300 MHz): δ 4.66 (t, J=6.6 Hz, 2 H); 4.61 (t, J=6.6 Hz, 2H); 4.16 (s, 2 H); 3.95 (p, J=6.6 Hz, 1 H); 2.63 (t, J=12.5 Hz, 2 H); 2.39 (tt, J=11.7, 3.7 Hz, 1 H); 2.20 (s, 3 H); 1.60 (d, J=12.5 Hz, 2 H); 1.46 (s, 9 H); 1.44-1.28 (m, 2 H).

Workup

  1. washwas washed with MeOH/DCM
  2. washthe product eluted with 2M NH3/MeOH
  3. customThe resulting oil was purified by column chromatography (Si—PCC, MeOH/DCM, 0-20%)

Sources & evidence

ORD record
ord-5e915f63e8864685a5179d61bf717777
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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