Chlorotrimethylsilane → HCID 22116264, compound

HRID 888736Notes

Reaction equation

HRID 888736 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 mixture of 1-aminoadamantane-3-ol (5.00 g; 30.0 mmol) and potassium carbonate (6.20 g; 45 mmol) in 150 ml of tetrahydrofuran is added benzylchloroformate (4.70 g, 33.0 mmol) in dropwise fashion over a 10 minute period. The mixture is then stirred at room temperature for 2 h and then partitioned between ethyl acetate and water. The product is then extracted into the ethyl acetate and the aqueous layer is washed twice with ethyl acetate (100 ml). The combined organic layers are then washed successively with 100 ml of aqueous 2 N sodium hydroxide, water and brine, dried over sodium sulfate, filtered and concentrated (rotovap/pump) to provide 1-benzylcarbamoyladamantane-3-ol as a white solid in 85% yield. 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-d297b00eef1f46aa9a2ef9dc9ea1b135
Source dataset
uspto-grants-2012_08
Patent number
US08252751B2

Reaction notes

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