(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-cyclopropylbut-3-en-2-ylcarbamate → (S)-1-(tert-butyldimethylsilyloxy)-3-cyclopropylbut-3-en-2-amine

HRID 627245Notes

Reaction equation

HRID 627245 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([NH:16]C(=O)OC(C)(C)C)[C:11]([CH:13]1[CH2:15][CH2:14]1)=[CH2:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(Cl)Cl.[Br-].[Zn+2].[Br-]>[Si:1]([O:8][CH2:9][C@@H:10]([NH2:16])[C:11]([CH:13]1[CH2:15][CH2:14]1)=[CH2:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 89852294(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-cyclopropylbut-3-en-2-ylcarbamate2×

Product 1

HCID 89851324(S)-1-(tert-butyldimethylsilyloxy)-3-cyclopropylbut-3-en-2-amineYield 96.3%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-cyclopropylbut-3-en-2-ylcarbamate (Intermediate 233, 6.77 g, 19.82 mmol) in DCM (100 mL) at room temperature was added zinc bromide (17.86 g, 79.28 mmol). The reaction mixture was stirred overnight at room temperature. Another 1 eq of zinc bromide was added. After several hours the reaction mixture was filtered and washed with saturated sodium bicarbonate. The resulting emulsion was filtered through a nylon filter and the layers were separated. The organics were dried over magnesium sulfate, filtered and concentrated to afford the title compound as a yellow oil (4.61 g, 96%).

Workup

  1. filtrationAfter several hours the reaction mixture was filtered
  2. washwashed with saturated sodium bicarbonate
  3. filtrationThe resulting emulsion was filtered through a nylon
  4. filtrationfilter
  5. customthe layers were separated
  6. dry with materialThe organics were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-dfe8c30f604f4108b5903b45896d8c99
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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