Chlorotrimethylsilane → HCID 22116264, compound

HRID 1045314Notes

Reaction equation

HRID 1045314 reaction equation
[CH2:1]([NH:8][C:9]([C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][C:13]([OH:21])([CH2:14]3)[CH2:12]1)[CH2:18]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([N:26]=[C:27]=[O:28])([CH3:25])([CH3:24])[CH3:23].C[Si](Cl)(C)C>C(Cl)Cl>[C:22]([NH:26][C:27]([O:21][C:13]12[CH2:19][CH:17]3[CH2:16][CH:15]([CH2:20][C:11]([C:9](=[O:10])[NH:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)([CH2:18]3)[CH2:12]1)[CH2:14]2)=[O:28])([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 62412tert-Butyl isocyanateHCID 22116258HCID 22116258, compound

Product 1

HCID 22116264HCID 22116264, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a clear solution of 1-benzylcarbamoyladamantane-3-ol (1.00 g: 3.32 mmol) and tert-butylisocyanate (380 μl, 3.32 mmol) in 30 ml of methylene chloride is syringe-added trimethylsilyl chloride (20.0 μl, 0.17 mmol). This reaction is then stirred at room temperature for 18 hours, concentrated (rotovap) and purified on silica gel employing a SIMS/Biotage apparatus and 20% ethyl acetate in hexane as eluent to yield 3-[[(tertbutylamino)carbonyl]oxy]-1-benzylcarbamoyladamantane as a white solid in quantitative yield.

Workup

  1. concentrationconcentrated (rotovap)
  2. custompurified on silica gel employing a SIMS/Biotage apparatus and 20% ethyl acetate in hexane as eluent

Sources & evidence

ORD record
ord-191865fd4d974befb29b1608fa61f5a0
Source dataset
uspto-grants-2013_10
Patent number
US08569250B2

Reaction notes

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