Triethylamine → Benzyl-(3R,4R,5S)-3-[(tert-butoxycarbonyl)amino]-4-{[tert-butyl(dimethyl)silyl]oxy}-5-methylpiperidine-1-carboxylate

HRID 1499568Notes

Reaction equation

HRID 1499568 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C@H:8]1[C@H:13]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[C@@H:12]([CH3:22])[CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH2:24]([O:31][C:32](ON1C(=O)CCC1=O)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>C(Cl)Cl.CCOC(C)=O>[CH2:24]([O:31][C:32]([N:10]1[CH2:11][C@H:12]([CH3:22])[C@@H:13]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:16])[CH3:17])[C@H:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:23])[CH2:9]1)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 70901078tert-Butyl N-[(3R,4R,5S)-4-[(tert-butyldimethylsilyl)oxy]-5-methylpiperidin-3-yl]carbamate

Product 1

HCID 90279471Benzyl-(3R,4R,5S)-3-[(tert-butoxycarbonyl)amino]-4-{[tert-butyl(dimethyl)silyl]oxy}-5-methylpiperidine-1-carboxylateYield 38%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl-((3R,4R,5S)-4-{[tert-butyl(dimethyl)silyl]oxy}-5-methylpiperidin-3-yl)carbamate (3.2 g, 9.4 mmol) (40% purity) in DCM (25 mL), N-(benzyloxycarbonyloxy)succinimide (2.6 g, 10 mmol) was added, followed by triethylamine (1.4 mL, 10 mmol). The mixture was stirred for 16 h at room temperature. The reaction mixture was then diluted with EtOAc, washed with water and brine and dried over Na2SO4. The solvent was evaporated under reduced pressure and the resulting crude product was purified by silica gel chromatography eluting with 25% EtOAc in hexanes to give the sub-title compound as a white solid (1.71 g, 38%). LCMS calc. for C25H42N2O5SiNa (M+Na)+ m/z=501.3. found 501.0.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. customThe solvent was evaporated under reduced pressure
  4. customthe resulting crude product was purified by silica gel chromatography
  5. washeluting with 25% EtOAc in hexanes

Sources & evidence

ORD record
ord-7b1b407b9f114402b6e65a871bb81164
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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