Sodium hydride → HCID 71270810, compound

HRID 1525890Notes

Reaction equation

HRID 1525890 reaction equation
[Si:1]([O:8][CH2:9][C:10]1([N:13]([CH2:18][C:19]2([OH:32])[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[C:14](=[O:17])[CH2:15]Cl)[CH2:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+]>O1CCCC1>[Si:1]([O:8][CH2:9][C:10]1([N:13]2[CH2:18][C:19]3([CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)[O:32][CH2:15][C:14]2=[O:17])[CH2:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86725425HCID 86725425, compound

Product 1

HCID 71270810HCID 71270810, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-((N-(1-(((tert-butyldimethylsilyl)oxy)methyl)cyclopropyl)-2-chloroacetamido)methyl)-4-hydroxypiperidine-1-carboxylate (1.511 mmol) in anhydrous tetrahydrofuran (20 mL) was added 60% sodium hydride in mineral oil (3.02 mmol) in one portion. The suspension was heated at reflux for 1 h then cooled, quenched with water (1 mL), and evaporated to dryness in vacuo. Purification of the residue by flash chromatography (20-80% ethyl acetate in hexanes) afforded the title product (450 mg, 64% yield) as a colorless oil. MS(ES)+ m/e 455.3 [M+H]+. 1H NMR (400 MHz, CDCl3) δ ppm 0.03 (s, 6 H) 0.76-0.98 (m, 13 H) 1.47 (s, 11 H) 1.70-1.89 (m, 2 H) 2.90-3.18 (m, 2 H) 3.35 (s, 2 H) 3.70 (br. s., 2 H) 3.85 (br. s., 2 H) 4.11 (s, 2 H).

Workup

  1. temperatureThe suspension was heated
  2. temperatureat reflux for 1 h
  3. temperaturethen cooled
  4. customquenched with water (1 mL)
  5. customevaporated to dryness in vacuo
  6. customPurification of the residue by flash chromatography (20-80% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b6aeb62b619346dd83291b016c7d58a6
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

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