Imidazole → Tert-butyl 3-(tert-butyldiphenylsilyloxy)-1,1,1-trifluoropropan-2-ylcarbamate

HRID 2279557Notes

Reaction equation

HRID 2279557 reaction equation
[F:1][C:2]([F:15])([F:14])[CH:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:4][OH:5].N1C=CN=C1.[C:21]([Si:25](Cl)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([CH3:24])([CH3:23])[CH3:22]>C(Cl)Cl>[Si:25]([O:5][CH2:4][CH:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:11])([CH3:10])[CH3:12])[C:2]([F:14])([F:15])[F:1])([C:21]([CH3:24])([CH3:23])[CH3:22])([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 14377427tert-Butyl (1,1,1-trifluoro-3-hydroxypropan-2-yl)carbamate

Product 1

HCID 68294202Tert-butyl 3-(tert-butyldiphenylsilyloxy)-1,1,1-trifluoropropan-2-ylcarbamateYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 340 (240 mg, 1.047 mmol) in DCM (3 mL) at 0° C. under nitrogen was added solid imidazole (71.29 mg, 1.047 mmol) followed by tert-butylchlorodiphenylsilane (272.3 μL, 1.047 mmol) neat by syringe. After 4 h the reaction was diluted to 30 mL with DCM and was washed 2N HCl (2×30 mL) and satd. aq. NaHCO3 (2×30 mL). The organic phase was isolated, dried (MgSO4), filtered and concentrated to afford 460 mg (94%) of tert-butyl 3-(tert-butyldiphenylsilyloxy)-1,1,1-trifluoropropan-2-ylcarbamate a white solid (342).

Workup

  1. washwas washed 2N HCl (2×30 mL)
  2. customThe organic phase was isolated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ee4091af99234a4b928349210501b8f1
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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