Water → (1S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclopent-2-enylamine

HRID 402534Notes

Reaction equation

HRID 402534 reaction equation
[N:1]([C@H:4]1[CH2:8][C@@H:7]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH:6]=[CH:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.[Cl-].[Na+]>O1CCCC1>[C:13]([Si:10]([CH3:12])([CH3:11])[O:9][C@@H:7]1[CH2:8][C@H:4]([NH2:1])[CH:5]=[CH:6]1)([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 11776TriphenylphosphineHCID 86639599((1R,4S)-4-Azido-cyclopent-2-enyloxy)-tert-butyl-dimethyl-silane

Product 1

HCID 59224828(1S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclopent-2-enylamineYield 106.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

934 mg (3.90 mmol) of ((1R,4S)-4-azido-cyclopent-2-enyloxy)-tert-butyl-dimethyl-silane (35) were dissolved in 16 mL of tetrahydrofuran and 1.13 g (4.29 mmol) of triphenylphosphine were added. After the addition of 2 mL of water, the reaction mixture was stirred at room temperature, until the reaction was complete. Sat. sodium chloride solution was added, the layers separated and the organic layer was evaporated in vacuo. The crude product was purified by silica gel chromatography to yield 890 mg of the title compound (36). Rt=1.02 min (Method C). Detected mass: 214.3 (M+H+).

Workup

  1. customthe layers separated
  2. customthe organic layer was evaporated in vacuo
  3. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-22d08b3ff24741c9ba8ea844fc34e97e
Source dataset
uspto-grants-2014_06
Patent number
US08742116B2

Reaction notes

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