Sodium Azide → 1-Azido-5-{[tert-butyl(dimethyl)silyl]oxy}-3-phenylpentan-3-ol

HRID 271991Notes

Reaction equation

HRID 271991 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([OH:15])[CH2:12][CH2:13]Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N-:22]=[N+:23]=[N-:24].[Na+]>CN(C=O)C.CCOC(C)=O>[N:22]([CH2:13][CH2:12][C:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([OH:15])[CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[N+:23]=[N-:24]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 598359701-{[Tert-butyl(dimethyl)silyl]oxy}-5-chloro-3-phenylpentan-3-ol

Product 1

HCID 598359641-Azido-5-{[tert-butyl(dimethyl)silyl]oxy}-3-phenylpentan-3-ol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-{[tert-butyl(dimethyl)silyl]oxy}-5-chloro-3-phenylpentan-3-ol ((5.2 g, 15.7 mmol) and NaN3 (7.8 g, 120 mmol) in 50 mL DMF was stirred for 24 h at 65° C. The reaction mixture was then diluted with EtOAc, washed with water, dried, filtered and evaporated in vacuo to provide 1-azido-5-{[tert-butyl(dimethyl)silyl]oxy) 3-phenylpentan-3-ol in quantitative yield as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.40-7.32 (m, 4H), 7.24 (m, 1H), 4.89 (s, 1H), 3.72 (dt, 1H, J=10.3, 3.9 Hz), 3.47-3.36 (m, 2H), 2.97 (ddd, 1H, J=12.3, 10.1, 5.5 Hz), 2.24-2.10 (m, 2H), 2.07-1.93 (m, 2H), 0.86 (s, 9H), −0.02, (s, 3H), −0.09 (s, 3H); ESI-MS 358 (M+Na).

Workup

  1. washwashed with water
  2. customdried
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-2f44129d0daf485981948cdab876b52c
Source dataset
uspto-grants-2008_11
Patent number
US07452992B2

Reaction notes

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