tert-Butyldimethylsilyl chloride → 3-(Benzyloxycarbonylamino)-1-(((1,1-dimethylethyl)dimethylsilyl)oxy)-cyclobutane

HRID 465761Notes

Reaction equation

HRID 465761 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH2:15][CH:14]([OH:16])[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>N1C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH2:15][CH:14]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 19794302Benzyl (3-hydroxycyclobutyl)carbamate

Product 1

HCID 197943263-(Benzyloxycarbonylamino)-1-(((1,1-dimethylethyl)dimethylsilyl)oxy)-cyclobutaneYield 94.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-(Benzyloxycarbonyl)-3-amino-1-cyclobutanol (2.22 g, 10 mmol) from Step B and t-butyldimethylsilyl chloride (4.8 g, 32 mmol) were combined in 25 mL of anhydrous pyridine and the cloudy suspension was stirred over the weekend at ambient temperature, under a nitrogen atmosphere. After 65 h, the solution was concentrated in vacuo at 35°-40° C. The concentrate was diluted with 250 mL of methylene chloride and the methylene chloride solution was washed with 3×100 mL of water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue (3.9 g) was purified on a 1.0×45 cm silica gel column eluted @5 psi with 100 mL of hexane, followed by 200 mL of 10% acetone in hexane to give 3.16 g (88% yield) of the title compound; MS DCI-NH3M/Z: 336 (M+H)+, 353 (M+NH4)+ ; 1H NMR (CDCl3) δ - 0.03 (s, 6H), 0.83 (s, 9H), 1.75 (m, 2H), 2.68 (m, 2H), 3.69 (m, 1H), 3.93 (m, 1H), 5.06 (s, 2H), 7.30 (m, 5H).

Workup

  1. concentrationthe solution was concentrated in vacuo at 35°-40° C
  2. additionThe concentrate was diluted with 250 mL of methylene chloride
  3. washthe methylene chloride solution was washed with 3×100 mL of water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue (3.9 g) was purified on a 1.0×45 cm silica gel column
  7. washeluted @5 psi with 100 mL of hexane

Sources & evidence

ORD record
ord-2ac71d8853b142f887200c410f14ff51
Source dataset
uspto-grants-1992_10
Patent number
US05153352

Reaction notes

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